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Washington Goes Hollywood, For Laughs; A Funnyman With A Tough Job. Aired 7-8p ET

Aired April 30, 2016 - 19:00   ET


[19:00:11]JOHN BERMAN, CNN ANCHOR: Tonight fabulous meets famous meets Washington. Who will survive? Who will thrive? Who will laugh? Here's a preview of coming attractions.


PRES. BARACK OBAMA (D), UNITED STATES: This is no ordinary dinner. This is a big (bleep) meal.

UNIDENTIFIED FEMALE: I want to welcome all of you to the White House Correspondents' Association Dinner.

OBAMA: Tonight when Washington celebrates itself. Somebody's got to do it. Supreme Court ruled that the donor who gave Ted Cruz $6 million was just exercising free speech.

UNIDENTIFIED MALE: Yes, the kind of speech like this, I just wasted $6 million.

UNIDENTIFIED MALE: He is released the black in.

OBAMA: Well, that's a legacy. And Donald Trump is here. Still.

UNIDENTIFIED FEMALE: Your gray hair is at 85 percent. Your hair is so white now it can talk back to the police.

ANNOUNCER: The White House Correspondents' dinner.

UNIDENTIFIED MALE: What is this thing?

OBAMA: Welcome to America.

ANNOUNCER: Starts right now. The show is not yet rated.


BERMAN: Welcome to a night unlike any other where people go to see and be seen and then tweet about it. There's Aretha Franklin for God's sake. Tonight when Hollywood stars political players and journalists wearing borrowed clothes are all walking the red carpet. President Obama and the First Lady will be there. Larry Wilmore from "The Nightly Show." Members of Congress, campaigns, pop culture, plus real life journalists and the people who play them on TV. It's a night to eat, tell jokes and help raise money for a noble cause, scholarships and awards to support good journalism. Good evening, everyone. Welcome to CNN's Special Coverage of the

annual White House Correspondents' Dinner. I'm John Berman. None fabulous enough to be there but available enough to work. This hour, it is all about the glamour. Let's get right to that glamour. We're going to the red carpet right now. The regent of the red carpet.

CNN political reporter Sara Murray is there with some very special guests. Sara.

SARA MURRAY, CNN POLITICAL CORRESPONDENT: We do have some very special guests to start off. The night tonight, John. Tonight, Donald Trump will be skipping the dinner but he sent his most capable surrogates for here with Don Jr. and his lovely wife. Thank you guys so much for joining us.



MURRAY: So, tell me, this is your first time at the dinner, did you have any reservations knowing in the past your dad has been the butt of a couple of the jokes.

No, listen, I think if there's anyone that can make fun of ourselves, it's my father, it's me, it's our family. I mean, that's where we are. I mean, you see his sense of humor. You've seen him coming out of the campaign trail. And he's a lot more reserved there than he is at home when we're having fun around the table. So, you know, we're ready. We realizes all in good fun and we can dish it out and we can take it.

MURRAY: So, what's is going to be like for you, if President Obama is up there poking fun at Donald Trump, are you going to be laughing at those jokes or is it going to be stern face?

V. TRUMP: I don't think I'm going to be laughing at them.

TRUMP, JR.: I'll be laughing at them. I'm okay with it. I'll have a good time. Maybe he'll give me more material I can recycle on my father when we're alone.

MURRAY: Now, I'm sure you'll going to be a popular dinner guest tonight. There are many people who want to know more about your father's candidacy. But who do you guys want to meet tonight? What celebrity are you going to see and just geek out off?

TRUMP, JR.: Honestly, I'm just here to hang out with some of the friends I've met along the trail. I mean, I'm pretty new to this politics thing. I've been in this business for 14 days now. So we're having a good time. We're learning a lot. It's just been amazing to be a fly on the wall in this experience. I mean, it's really incredible.

MURRAY: So, no top celebrity sighting -- Bryan Cranston is going to be there. He's a guest of CNN. TRUMP, JR.: You know, honestly it's one of those things that I guess

we're sort of used to it. You know, when I think about my father it's probably about as famous as it gets anywhere in the world right now and I see him on a daily basis. So, you know, we're not necessarily one for celebrity. When it's the guys I've learned a lot on the campaign trail. For the people that have been really good to us along the way. I want to see them and catch up with them and the friends I've made. So, we're not really celebrity chasers.

V. TRUMP: And also being away from five kids, being out, dressed up. Get some alone time.

TRUMP, JR.: Yes. It's a very good point. Because mama over here taking care of the five kids while I've been on the campaign trail has been a little bit neglected.

MURRAY: So, if your dad is successful if he does win in November if he's the president, what's this dinner going to look like next year?

[19:05:04] TRUMP, JR.: Well, you know, I imagine the conservative tables will be a little bit more up front and the liberal publications will be a little bit more in the back. I think, you know, it's the opposite of the way it would be right now. But no, listen it will be a good time, it will be a good party. I mean, everyone has seen the way he is. And you know, I think seeing some of the roasts that he's done whether it's been as a recipient or as a giver. I think it will be a lot of fun.

MURRAY: Will he write his own joke?

TRUMP, JR.: I think he would right a lot. I mean, listen that's not the easiest thing in the world to do. I mean, one of the things I see is when people try to do it sometimes themselves. You know, I don't know of anyone and that platform that has done it by themselves. But I think he'd have a lot of input. A really most of it is really about the delivery. And no one is going to do it better than him on that one.

MURRAY: You definitely has the performance there. Thank you guys so much. We really appreciate it.

TRUMP, JR.: Thank you.

V. TRUMP: Thank you.

MURRAY: Have a great time tonight.

V. TRUMP: Thank you.

MURRAY: All right. John Berman, you heard them there. They're not worried about the tone of a dinner tonight. But they are pretty confident this is going to look very different a year from now. Back to you.

BERMAN: And they don't want to meet Bryan Cranston.

MURRAY: I don't understand that at all. I don't understand that.

BERMAN: All right.

MURRAY: I think they're just trying to play it cool.

BERMAN: Sara Murray, great to see you, bill out there finding other fabulous people who were there. Thank you so much for working on this night that should be all about fun.

MURRAY: Of course.

BERMAN: Thanks so much, Sara.

All right. I'm with an amazing line up of guests, experts in politics, fashion history comedy power gossip, and money. I'm joined by Kate Andersen Brower. She is the author of "The Residence" about life inside the White House. She also just published "First Women" about America's model first ladies. Also with us, Brad Jenkins, executive producer at Funny or Die. And Lizz Winstead, a co-creator and former head writer of "The Daily Show."

Guys, this is a historic White House Correspondents Dinner. President Obama, his final dinner there. President Obama who has had some very memorable moments at these dinners. You know, so I think people are expecting very, very big things. Lizz, your thoughts on the night.

LIZZ WINSTEAD, CO-CREATOR AND FORMER WRITER, "THE DAILY SHOW": You know, I just keep thinking back to 2011 when he talked about Donald Trump and Donald Trump was the big joke. And it's kind of like, wow, one of the parts -- it might be a part of his administration that he can admit he was wrong. But nobody cares about Donald Trump and guess what, apparently America cares about Donald Trump.

BERMAN: Now, look, you're talking about 2011, that was the weekend that President Obama launched the raid that killed Osama bin Laden. It's hardly been underway and pretty much complete about the time that President Obama was speaking to the crowd roasting Donald Trump. Brad, Donald Trump was in the audience --


BERMAN: -- not laughing. In some ways it may be a most famous White House Correspondents Dinner. Pressure on the President to top that tonight?

JENKINS: I don't think he can have to really top that. I think Donald's hew of orange got even oranger from folks that were there and saw it in person. No, I don't think that he'll ever top that. I think that he'll have a lot of fun tonight. I think mostly for me, it's about the Obama legacy. I think it's a lot about, you know, rapping up what is a pretty historic presidency. I think Trump will get a few jokes. But I think he's going to focus more on what he was able to accomplish in eight years.

BERMAN: We're looking at Carmelo Anthony by the way who has the night free because the Knicks aren't in the playoffs. (LAUGHTER)

So, he can go to the White House Correspondents Dinner. And yes, interesting. All right. Kate, all right, I want to ask you, presidents and first ladies, have mixed emotions about this dinner is my experience. They have to sit up there on the podium for three hours. Surrounded by people who largely grill them night in and night out. And have to pretend like they like it.

KATE ANDERSEN BROWER, AUTHOR, "FIRST WOMEN": Uh-hm. Yes, they usually dread it I think. You know, that's why it was so interesting in 2005 when Laura Bush came out and made this joke about being a desperate house wife and how she and Lynn Cheney would watch "Desperate Housewives" at 9:00 when the President was asleep. And it's really a moment for them to shine. I don't know if Michelle Obama will choose to do that. She has a great sense of humor friends say. If she'll come out and say anything, but I think that President Obama will leave it all on the field today. He'll just, you know, he has nothing to lose. And he's going to just -- he's so witty naturally. So it will be really interesting to see how far he takes this.

BERMAN: I got to name drop here for the first time -- about a hundred times for the course of the evening. But I interviewed Larry Wilmore and we'll going to show that interview. Larry told me, Brad, that the hardest part of the night will be sitting up there next to Michelle Obama --


BERMAN: The whole time before he's about to deliver his comedy routine.

JENKINS: Well, from what I hear, it's the hardest gig to book in the Correspondents Association because the comedian has to go after the President. And it's, you know, the President has you just said, he is, you know, if the President thing didn't work out for him he could have been a comedian. He's got a really great sense of set up. Punch line. And it's fun to watch the President doing jokes. I think the public loves to see that. I love Larry. I love his team. I love Lewis K. And I hope that -- I think he's going to do a great job. I think he's a great kind of end note to the President's final Correspondents Dinner.

BERMAN: You know everyone in the business. You've been talking to people writing the jokes.

WINSTEAD: Yes. I know some people writing the jokes. And I think that it's right. And I think we were talking about it's just emotionally empathetical for a performer like myself to see the head liner go first.

BERMAN: Yes. The President, the President goes first.

WINSTEAD: The President goes first. Right.


WINSTEAD: But then you realize a comic who is on their chops is sitting there with their cards being like, not doing that. Like literally during the dinner. That's going out. The President is, OK, I just killed that joke, I have something exactly like that. Because so many times they don't go to the White House with new material.

BERMAN: Right.

WINSTEAD: Because they want to keep it fresh. And so, it's like, I think it would be harder for the president to be like, well you stepped on that one. You know, like, no, the President has to have like, the freshest material.

BERMAN: That's right. You were in the White House. I mean, while this was going on. Any sense of the preparation inside the White House to get the President ready?

JENKINS: Yes. I mean, I will say as fun as this is this is probably the least important thing the president is doing.

BERMAN: I have a hard time believing that.

JENKINS: Perhaps this month let alone this year. But not, I mean, we have an incredible team of speechwriters, my colleague David Litt who is now the head writer of "Funny or Die" has honed the speech for the past few years. He tells me it starts about three weeks before the speech. They start with about 100 jokes. And as Liz says a lot of these jokes come from some of the best comedians in the business. Very stealthy communications that happen.


JENKINS: And those 100 get whittled down to say, 50 or so. Those get presented to the President. And then he mostly just, you know, he selects the ones he likes and that gets down to about 35 or 40. But it's just like anything the President wants to make sure that it's the best that it can possibly be. He takes it seriously. And yes, it's a fun process.

WINSTEAD: Well, it's comics, too, when they watch the Correspondents Dinner and the President has a great joke. Comedians are just so spiteful, right?


They're like that guy has the greatest joke about that he'll never do it again. It's a no act. I didn't write it. I can't have it. It's like, you know, it's like watching somebody do great things and then have that stuff just go away.

BERMAN: Kate, last word here before we go to break. Do the presidents care? I mean, how much do they care about being funny do you think?

BROWER: Oh, I mean, I think it would be embarrassing if they bombed, you know.

BERMAN: Right.


BROWER: I think they want to do well. And I am going to name drop here, I'm good friends of Carol Lee who is the president of the White House Correspondents Association. And she said she picked Larry Wilmore because he is up and coming and he's not afraid to be searing and talk about race and these controversial issues. It's harder to get someone like Tina Fey, Amy Poehler, or someone who is really a stablished super famous to do this gig, I think.

BERMAN: We can all name drop as much as we want tonight. Because we're not there. I think the deal we can make with each other is we should feel free to say whatever we want throughout the evening.

Guys, stick around. As we said, tonight will be the President's final Correspondents Dinner. In a moment we'll going to look back at some of his best moments including some jokes really that may have changed history.



OBAMA: Of course, the White House Correspondents Dinner is known as the prom of Washington, D.C. A term coined by political reporters who clearly never had a chance to go to an actual prom.


BERMAN: That was President Obama just delivering one of the many jokes he has over his seventh Correspondents Dinners. This is his final White House Correspondents Dinner. Is he saving the best for last? You won't believe what we see in other red carpet so far. Carmelo Anthony, Will and Jada Pinkett Smith. We saw Michael Kelly, the dude from House of Cards. None of whom have worked in journalism or the White House.

But our Jeff Zeleny has had a chance to speak to someone who is currently working in the White House. The current White House Press Secretary Josh Earnest.


JEFF ZELENY, CNN CORRESPONDENT: This is the President's last White House Correspondents Dinner. I'm sure he's relieved. But will he be different tonight? Will he be funnier, more serious?

JOSH EARNEST, PRESS WHITE HOUSE SECRETARY: He's going to be funny. And he's not going to pull any punches. And this is an opportunity he always enjoys. Put on a tux, poke a little fun at himself. Poke a little fun at Washington. And poke a little fun at his adversaries too.

ZELENY: How many joke were left on the cutting room floor this year?

EARNEST: Lots. Lots. This is a process of thinning the herd. So, we start out with a large pile. And we sift through to find the very best ones.

ZELENY: Any Donald Trump comments tonight? I mean, we all remember the night when Mr. Trump was in the room and he talked about him and in 2011 I believe that was.

EARNEST: That's right. But after all that we've all been through to the course of last year, it would not be the White House Correspondents Dinner if Mr. Trump ended up on the cutting room floor.

ZELENY: So, preview tonight you can tell us right now, Donald Trump will be a theme of the President's address?

EARNEST: It would not be the same if we left him out.

ZELENY: OK. Anything from Mrs. Obama, are we going to hear from her tonight?

EARNEST: I don't think so. She usually participates in the presentation of the awards, the scholarships. But no speeches for her tonight.

ZELENY: What -- what do you think this dinner would look like? This White House Correspondents Dinner, you're a veteran of all this. If Donald Trump were actually up on the bias as president?

EARNEST: Well, that's a provocative question. He certainly looks good in a tux. He'd be comfortable up there. People would be on the edge of their seat to see what he had to say. But I don't know, I have a sneaking suspicion that's not likely to happen.

ZELENY: Does the President feel responsible at all for Donald Trump's rise by poking his finger directly into his eye in 2011. Some people close to Donald Trump has said that's why he decided to run.

EARNEST: I don't think there's any denying the President got the better end of that exchange. I don't know if that's --

ZELENY: Are you sure about that?

EARNEST: Yes. I think that's right. I don't think anybody knows exactly why Mr. Trump is running for president. Or what's motivating him.

ZELENY: Millions of people voting for him though, so we'll let them make that final decision.

EARNEST: That's exactly right. That is the beauty of the process the American people get to decide.

ZELENY: All right, Josh. Thank you very much. We'll see you out there.

EARNEST: Nice to see you.


BERMAN: All right. Thanks to Jeff Zeleny for that. A promise from Josh Earnest that President Obama will bring up Donald Trump during his speech. So stay tuned for that. So the President will be there. Politicians Hollywood celebrities. But one person in that room shines above all others, and Sara Murray is with him right now -- Sara. Oh, look and Kate Bolduan is there too.

MURRAY: I think I have some faces that you recognize with me on the red carpet. We have Kate Bolduan and Wolf Blitzer. They have been party hoppings. Thank you guys for taking a minute to come chat.

KATE BOLDUAN, CNN ANCHOR: Totally party hoppings. Sorry, John.

MURRAY: Yes, sorry John. OK, guys. Let's talk about what you guys have seen so far. What's going on at the party?

WOLF BLITZER, CNN ANCHOR: Well, we did see Senator Bernie Sanders. He's here with Jane. Jane was very lovely. She was very nice. And I think she's pretty happy to be here. What do you think?

BOLDUAN: She seemed okay to be here. Bernie Sanders very -- he seemed uncomfortable in the crowd.

MURRAY: It was little weird. That, you know that, you know, I wasn't here earlier, he may have come through the red carpet when Jeff was out here. But it's interesting that he's the candidate to come to this dinner, the outsider anti-establishment, anti-lobbying guy.

BOLDUAN: Absolutely. And it is also, as we've walked all these parties beforehand and we go into the parties, it is the strange mass of humanity, and you turn around and you see Tony Blinken, you see Steny Hoyer, you see Nancy Pelosi, you see Bernie Sanders, you see --

BLITZER: Senator Dianne Feinstein. We saw a lot of senators, a lot of members of the House.

BOLDUAN: And everyone is just kind of crushed together in one room. I've -- as many times as I've come, I'm still not sure what to make of it.

MURRAY: It's like a little too up close and personal with senators.

BOLDUAN: Very up close sometimes. Like, you're all in each other's personal space.

MURRAY: So, this is President Obama's last White House Correspondents Dinner. It may be a little poignant for him. What are you going to be listing for? What are you expecting from him tonight?

BLITZER: I think he's going to be a really funny. I have a little clue about what he's going to say.

BOLDUAN: What's the clue? BLITZER: And I can't share that with you. I have a confidentiality agreement. So, but I think you'll enjoy it. There will be a special moment that all of us will really enjoy. So, just get ready.

BOLDUAN: If everyone knows Wolf Blitzer, everyone knows what that means. It means it involves Wolf.

BLITZER: We will just watch it very closely.

MURRAY: OK. So what should we watch from the Trump children tonight? Donald Trump is not here. But Eric Trump is here, Don, Jr. Is that going to be awkward?

BOLDUAN: It can't be more awkward than when Donald Trump was here the last time.

BLITZER: I was here for that dinner too. He was at the table next to me. Yes.

MURRAY: Were you watching his face?

BLITZER: I was sort of sitting sort of off. I couldn't see his face. We saw his face later, you know, on TV. But --

BOLDUAN: He said though that he loved it.

MURRAY: He said he loved it. But are we -- do we believe that?

BOLDUAN: No. If I were the kids tonight, it's uh-hm, I think I read it in The Washington Post. I think the key is, you need to laugh harder and think it's funnier whenever they're making fun of you because that's the only way to survive it.

BLITZER: I think it will be fun.

BOLDUAN: Yes, it will be fun.

MURRAY: All right. Kate, Wolf, thanks for taking a moment to break from the party hopping and break from the dinner.

BLITZER: You look amazing tonight.

MURRAY: Oh, thank you, Wolf.

BOLDUAN: I told John I was not going to divulge secret. But the secret is John Berman made this dress for me.

BLITZER: Really?


MURRAY: You know, that guy has so many talent.

BLITZER: I don't see the return video. Is he wearing a tuxedo?

MURRAY: No, he's wearing a gown. (LAUGHTER)

All right. John Berman, I think we have a little bit of trolling from you co-host here. But look, we've got a big surprise coming. Wolf knows all about it. And we'll see that inside. Back to you.

BERMAN: It's awesome. Kate Bolduan clearly upgrading right there. And I can't tell you how happy I am for all of you that you're having so much fun out on the town tonight. Sarah, Kate, Wolf, thank you all so much.

All right. Throughout the evening we'll be asking you the audience to weigh in. We have questions for you. The first one is, who was the funniest of the last three presidents? Going to vote. Pollster answer. We'll going to have the results in just a little bit. We're going to take a quick break.

In just a moment, we'll going to go back to the red carpet as Hollywood meets Washington and Wolf Blitzer. Everyone likes to show off.



OBAMA: Welcome to the White House Correspondents Dinner. The night when Washington celebrates itself. Somebody's got to do it. And welcome to the fourth quarter of my presidency. It's true. That was Michelle cheering.



BERMAN: All right. President Obama in last year's White House Correspondents Dinner. The question for our panel right now, how funny is he? What do you think, Lizz?

WINSTEAD: I mean, I think he's really funny. And the thing that he does that is the hardest thing to perfect in stand-up is he understands the pause and the silence. It's like, you know, everyone is like, it's timing it's timing. But it's really waiting and he also pushes the envelope really, really far. Like he wasn't afraid to like, get bleep on the F-bomb. He wasn't afraid to like, you know, do things that are genuinely funny and part of the zeitgeist. Like he follows even like comedy trends and I think that that's really cool.

BERMAN: Are you sure Brad that you're not grading him on a curve here, you know, funny for presidents? Do you think he's genuinely funny?

JENKINS: It's a good point. I genuinely think he's funny.

BERMAN: You worked for him. Your employment depended on it.

JENKINS: Yes. I work in a comedy company now. So, I think on par and Lizz, you know, creator of "The Daily Show," she can speak to this. He's very funny. He's very good at this. And it's almost scary to me that this is something he's never really working on. Right? He's not working on jokes and presenting. Does it once a year and knocks the ball out of the park each and every year. So, it is -- it's a skill. I mean, I think Louis C.K. took him 20 some years to get to where he is today. And, you know, I'm not saying President Obama is going to be the next Louie C.K.

WINSTEAD: But how amazing as he did? Like his post presidency, everyone is speculating -- I just want a late night show.

BERMAN: There was an F. Campbell right there. For party of five fans like we saw on F. Campbell. We don't know who that is. But you're looking over a shoulder right now.

JENKINS: She's Nina Dobrev, John. Nina Dobrev. Star of the "Vampire Diaries."

BERMAN: Thank God you're here. That's all I could say. Thank God you're here. Kate, funny presidents. It's my opinion that we always say whoever the president is, oh, this president loves to tell jokes. I mean, great that I wasn't alive during, you know, the Calvin Coolidge administration. But I kind of think we always like to pretend that our presidents can command a roof.

BROWER: Uh-hm. Like W. people think was really funny too in a different way of making fun of himself and how he couldn't pronounce nuclear and all that.


Obama I think is funny in a different way, it's like the timing that he has down path. Like he made that joke about his birth certificate and he showed a video from the Lion King and said the place of my birth. And then he said, FOX News this is just a joke.


BROWER: You know, and he was actually addressing the crowd and kind of bringing them in in a way that I think is like a very natural for him. So I think he's one of the funniest we've had recently.

BERMAN: You looking right now at the people are voting right now and they're saying President Obama is the funniest of the last three presidents. Every pollster I know will warn you that it's very likely that there's a lot of people in Washington tonight who want to see the president speak. Right? A lot of people want to see the President speak so they probably think he's funny to begin with. We want to talk a lot more about this guy and we'll keep -- no, I played "Jeopardy" with her. Ok?

JENKINS: Oh, yes.

BERMAN: Another name drop. Now I'm winning name drops. She was on the "Jeopardy" game I was on right there. She's very very nice. I'm a big giant fan. BROWER: Her?

BERMAN: Yes, I mean I won. But she's very very smart.

WINSTEAD: That was a good drop on top of a drop.


You know, wow!

She seemed like she had some intellect.

BERMAN: All right. We're going to go to break right now. Next, the other guy who will be telling jokes tonight Larry Wilmore. Will the "Late Night" host upstage the President? We'll get his thoughts when our coverage continues.



[19:34:48] WANDA SYKES, ACTRESS: You know, even in the media, you know, you guys have been very favorable towards the President. You know, it's funny to me that they've never caught you smoking but they somehow always catch you with your shirt off.


BERMAN: Some observations from Wanda Sykes. Welcome back to CNN's live coverage of the White House Correspondents Dinner. President Obama will not be the only one telling jokes tonight. The Correspondents Dinner featuring comedian Larry Wilmore which is a familiar face to all fans of Comedy Central. So, how do you make jokes about a president when he's sitting right next to you?


LARRY WILMORE, COMEDIAN: This is true. They're replacing Andrew Jackson who was a notoriously pro-slavery president as well as the most blood thirsty racist in the Jackson 5. True.


BERMAN (voice-over): Larry Wilmore knows it's way easier to win the nightly show crowd than woo what could be the fiercest most fickle audience in showbiz/Washington.

WILMORE: It's the most narcissistic room ever. Ever invented. Journalists politician and Hollywood and the President. There you go. That room could explode just from the narcissism alone.

BERMAN: But when it comes to the White House Correspondents Dinner, the explosion is worth the risk.

WILMORE: Something that I really wanted to do. And if I did it, I really did want to do it for this president. And I thought the time might have expired for that. So to sneak in there at the end is very cool.

What's happening, everybody?

BERMAN: The last such dinner for the first Black president starring an African-American comic.

WILMORE: Let's be clear about what Black face actually is.

BERMAN: Wilmore knows it is historic.

(on camera): You say you like the president. You say though, you didn't support him because of his policies --

WILMORE: Correct.

BERMAN: You supported him because he is Black.

WILMORE: Because of the policy that he's black.

BERMAN: How's he delivered on it?

WILMORE: I think he's been excellent. I think he's actually increased the policy of blackness over the past year and a half. I would say. He's released the blacken.

BERMAN (voice-over): A classic answer from the 54-year-old comic both deliberately funny and deadly serious.

WILMORE: If it feels like the nightly shows get a little reparative (ph), I totally I agree. I mean, at this point my writing staff just has to fill in the names.


They barely even show up the work anymore.

BERMAN: Fifteen months after he took over the time slot on Comedy Central vacated by Steven Colbert. "The New York Times" says Wilmore is less pre-occupied with humor than anyone else who has ever occupied a mock news chair.

WILMORE: Sometimes I'm not afraid to have to provide some glibness in a moment and to tell a story and to find humanity in the story and get the comedy out of that. Sometimes it works the other way around. It appears that Officer Slager immediately began the cover up Walter Scott's death.

When you're covering a story about a man getting shot in the back by cop when he's trying to run away. There's nothing funny in there. How do you cover something like that? How many of these murders aren't caught on camera.

BERMAN: He applies that same sometimes frank sometimes funny take to his views about the election. Which are admittedly liberal.

(on camera): Will you say your show trends left, trends more pro- Democratic policies and politicians?

WILMORE: I would say probably specially with the issues that tend to take on. Because a lot of them are cultural issues in that kind of name.

BERMAN: I'm going to throw out a candidate' name. There are five left. And I want to know if you have a first impression or a word that you associate with --


BERMAN: When I say Bernie Sanders, you say?

WILMORE: I say scrappy.

BERMAN: I say Ted Cruz, you say?

WILMORE: I say creepy.


BERMAN: I say Hillary Clinton.

WILMORE: Hillary Clinton? I say trying to find it.

BERMAN: John Kasich?

WILMORE: John Kasich, I'd say -- oh, man.

BERMAN: This is the problem with John Kasich right now. A lot of people are struggling.

WILMORE: That is the problem.

BERMAN: Donald Trump?

WILMORE: Donald Trump unbelievable. In every way.

Black people supporting Trump?


[19:39:04] BERMAN (voice-over): But when it comes to the Correspondents Dinner, Wilmore is promising all jokes delivered with the skill and experience of more than 20 years acting writing and producing on shows ranging from in living color to the Bernie Mac show.

WILMORE: I have a job.

BERMAN: To starring as the senior Black correspondent on the Daily Show.

UNIDENTIFIED MALE: Larry, what do you say to those people?

WILMORE: Oh, I don't know, John I would say they should probably go (bleep) themselves.


BERMAN: And this weekend, all targets are fair game.

WILMORE: Take a look at the whole Obama Saudi Arabia thing.

BERMAN: Including or especially the President.

(on camera): No free pass because it's his last dinner?

WILMORE: I have to keep it 100, come on, man. I mean, and this is the last dinner. What are they going to do? Not enough time to sic the IRS after me. Maybe I shouldn't say that on TV. But that's part of the fun. But it's all in good natured fun.

BERMAN (voice-over): The hardest part he says having to follow the President on stage, the President now experienced at telling jokes.

OBAMA: And Donald Trump is here. Still.


BERMAN (on camera): Do you think you'll laugh at him or you try not to laugh?

WILMORE: I'll completely laugh.

BERMAN: You don't want to lower expectations?

WILMORE: Well, no, no, no, I'll be a big great audience for him. Plus, it will help me not to be very nervous. You know, you get rid of that air, ha-ha-ha-ha, that's funny Mr. President, ha-ha-ha-ha-ha.


BERMAN: All right. We're back now with our panel. Joined this time by CNN political commentator Marc Lamont Hill. Well, Marc, you've been a panelist on "The Nightly Show" with Larry Wilmore. He is a different type of late night comic. It's not necessarily on a show joke joke joke joke joke.

MARC LAMONT HILL, CNN POLITICAL COMMENTATOR: Right. It's not like having a traditional standup comedian hosting the show and he's also not like Colbert who is in character. Instead like he said, he's somewhat -- at times, he's somewhat serious at times. But he's also flat out hilarious. And tonight, I think we'll see the full range of his comedy skill.

BERMAN: He has said -- he told Jake Tapper that he plans, he told me too, he plans to talk about race tonight. I mean, a lot of his jokes he admits on his show are about race. Well, I imagine that will be, you know, a theme here with the first, the last dinner for the first black president.

WINSTEAD: Yes, I think so. And I think that he -- it's always cool when you can get somebody who is a writer and a performer. Because when you are writing the material and helping craft it yourself, there's an intrinsic performance quality that comes. That's really great.

BERMAN: That's Marissa Meyer right there from Yahoo who took a pay cut. I think she made over $30 million instead of $40 million by this year. But she still did --

HILL: How big of her.

BERMAN: -- managed to get to the dinner tonight. I may have those numbers wrong. People in the industry love Larry Wilmore just because he worked his way up, you know, as a showrunner behind the scene. So, he appreciate the business of comedy tonight. But it is hard, right? I mean, it is hard for him to get up there after the President, Brad. And you know, he said he's frankly nervous about it.

JENKINS: I think all comedians are nervous to follow the President. I think what Larry has, I think Mark hit on it. You know, he's doing the show every night. So, he's very invested each night on what's happening. And so much of these bits are what's happening, what's topical, what's relevant. So, I think Larry is going to have a good night.

BERMAN: Kate, can you go too far?

BROWER: I think -- yes. Absolutely. I think there is like, a line there. You can't be too kind of out there. I think that's why. I mean, probably like to have someone like Chris Rock host one night. But he might be a little too controversial for them. You know, the room is inherently so strange. I mean, I remember going to the dinner and Richard Myers who was the chairman of the Joints Chiefs of Staff was my date and Pamela Anderson was at my table. And it's like, this amazing. And Kate Bolduan was saying, this early --

BERMAN: I call that Tuesday, by the way.


Tuesday at my house. Go ahead.

BROWER: Great. It's like the most bizarre thing. You know, you see this George Lucas and then like a congressman from Minnesota and then a staffer. And it's just a very strange juxtaposition of people.

BERMAN: That is Eric Trump behind this right now. The other Trump we heard from Donald Trump, Jr.

WINSTEAD: Is she with the other one's wife or is that his wife?

BROWER: That's his wife.

BERMAN: That's his wife, come on!


WINSTEAD: I don't know. You know.

BERMAN: Marc, I tried to press Larry on this. He told me he would make fun of the President.

HILL: Yes.

BERMAN: You know, he actually admires the President. I mean, Wilmore flat out says that he admires the President a lot. He thinks he's a historic figure. And he does poke fun about our show but he's not the most frequent target or the target he hits the hardest. Don't you think that it is owed to America tonight on the President's last Correspondents Dinner to have some of the best satire involving the President?

HILL: Absolutely. It's his patriotic duty. I think this is a tougher president to make fun of though. Because many presidents you can make fun of bodily features. You can make -- I mean, really, I mean, many presidents you can do that. Also he is so self- deprecating. He took on early on the stuff about being Muslim undercover --

BERMAN: Right.

HILL: About being a terrorists, about his birth certificate. About being grandiose. About being arrogant. Some of that stuff is hard to jab at him because he's already done a bit by the time you get up to the stage. I think what you'll hear a lot of from Wilmore are jokes about he said his unmitigated blackness right now. That he's just going out there and saying things he didn't say. Using slang he's never used before. And doing federal engaging in executive orders that he's never done before. That can be a joke.

[19:44:19] BERMAN: Is it hard to make fun of this president?

WINSTEAD: No. No. I mean I feel like good satire comes from talking about the policies and the hypocrisies. And I think that any president of the United States has come up in a system full of money in a system full of favors and a system full of many things. I mean, I'm a political satirists. You know, one of the first things that Obama did in this administration was go back on his prescription drug promise. Right? Like, I made jokes about that. So, there are tons of things.

HILL: We're running out of stuff. Particularly embarrassing, like two years ago, this has not been a particularly bad year.

WINSTEAD: And you're comparing him to people who are measuring their manliness on a campaign trail.

HILL: That's what I'm saying. The gold is on the other side.

BERMAN: The healthcare website works now as far as --


WINSTEAD: Exactly. All right. Guys stick around. There's a lot more to talk about. No

doubt many of tonight's jokes and Lizz was focusing on right there will feature the 2016 presidential race. Coming up, why some people might argue the race itself is nothing but a joke.

We will also go back to Sara Murray who is working the red carpet as all the stars arrive.



[19:49:36] CECILY STRONG, COMEDIAN: Hillary's campaign slogan is "It's Your Time" which I assume is what she says into a mirror when she's deadlifting 200 pounds.



BERMAN: Cecily Strong from last year. Welcome back to the CNN's coverage of the White House Correspondents' Dinner. We're join now on the panel by Donald Trump supporter Kayleigh McEnany and Ted Cruz supporter Buck Sexton. We have some Republicans in the House right now even though it is a Democratic president at his final Correspondents' Dinner.

Kayleigh, I think you're going to like this net part right now because Jeff Zeleny on the red carpet spoke to some other Donald Trump fans.


JEFF ZELENY, CNN CORRESPONDENT: What do you think the party will look like if Donald Trump wins?

SCOTTIE NELL HUGHES, TRUMP SUPPORTER: Well, we're going -- it's called diversity, something the Republican Party has never had. I'm talking about girl power on its girl power I think we'll actually say.

ZELENY: You actually worked in a White House, though, before. Right? So, tell me what you think Mr. Trump's White House will look like?

OMAROSA MANIGAULT, TRUMP SUPPORTER: Oh, I think that his White House will be a little bit different because his repositions (ph) are different. We have just -- seven years of Democratic policies and it's been very interesting that Donald has a clear vision about making this nation safe, about making sure that we secure our borders, making sure we have an economic prosperity for all Americans, creating new job opportunities as well.

ZELENY: But on a night like this, you know, some people still think Donald Trump is not the most serious candidate in the world. Do you think he has already proven them wrong, or does he still have to do that?

MANIGAULT: Listen, we're on the cusp of him becoming the Republican nominee. I mean, we're literally a sneeze away from getting to Cleveland, him claiming that nomination, and then we're going full steam ahead. Trump train to 1600 Pennsylvania Avenue.

ZELENY: Hillary Clinton, how tough of an opponent will she be?

MANIGAULT: Well, you know I work with the Clintons, and I think the secretary is be very tough. I think she is going to be a worthy opponent. And I think the great thing about this race is you have a very experienced politician, and then you have someone who is starting a movement, and he's not afraid to be tough. So you're going to see a showdown of the ages.

ZELENY: What do you think of the woman card that's been playing the last couple of days?

MANIGAULT: You're asking all this stuff. I have to talk about that with Katrina.

ZELENY: We already heard Katrina talked about it on our air a lot. What do you think?


MANIGAULT: You know, what? The great thing about this country is that we as women have been striving for equality. And so, since Hillary Clinton wants equality, she's going to get a level playing field in this race. He's going to go after her just as tough as he would. Kasich, he is going to go after our justice as he would Kasich. He's going to go after our justice tough as he would Ted Cruz. And that's what equality is, right? You don't want him to come into this race against her with kid gloves on. Right? That would undermine her power to be the first.

ZELENY: Do you think President Obama tonight will be tough on Donald Trump again, or do you think he's learned his lesson?

MANIGAULT: I was in the room the night that he had his moment with Donald Trump and it was very uncomfortable. Donald will not be there to defend himself, but believe me, he has thick skin. And it's about fun, it's about humor, and next year Donald will be delivering the laughs and the punch lines.


BERMAN: Jeff Zeleny asking all the tough questions to Omarosa, it appears than with Scottie Nell. It was interesting to see that discussion. She did that last year, Kayleigh, saying that next year Donald Trump will be delivering the punch lines.

KAYLEIGH MCENANY, TRUMP SUPPORTER: That would be the best White House Correspondents' Dinner ever to have Donald Trump up there. I cannot even imagine because he's so humorous on the campaign trail. To have him there I think would be just the best.

HILL: You believe that somebody writes his jokes, though. Because (INAUDIBLE) like I do, I'm the greatest comedian ever. It will be an unbelievable speech, I promise you it will be great. That's what I'm worried about.

MCENANY: But he is a pretty good comedian, right? I mean, come on, lying Ted, little Marco, he's hysterical. I think he might not need --

BERMAN: In this scenario, Marc Lamont Hill, I imagine you're not a Trump voter, but you're agreeing with Kayleigh that he has some communicabilities.

HILL: Yes. Some communicabilities but being able to be funny on the cap (ph) is different than writing 30 minutes of material for a crowd, particularly a liberal crowd. And I'm not saying the media is liberal but there are a lot of liberals annoying. Hollywood ain't laughing at him.

BERMAN: I'm so glad you brought that up, because this is a Hollywood crowd. This is a Democratic president which means, you know, look, if you bring your guests, the administration is going to be a more Democratic administration. You know, do the Republicans like watching the White House Correspondents' Dinner?

BUCK SEXTON, CNN POLITICAL COMMENTATOR: I've been to one, so I can tell you that I think generally speaking everyone has sort of a truce in mind. You know? And this year it would be a truce not just between Republicans and Democrats that everyone should be able to relax and laugh. And I do think that presidents in recent years, President Obama, President Bush before him, have done a good job making jokes that everybody can laugh at. It's not particularly rough or partisan, there's not the sort of stuff where you're laughing at people instead of laughing with them. Perhaps maybe with one exception with the Trump moment that was mentioned earlier.


[19:54:20] I think that was a little more, but again, Donald Trump can certainly take it. And within the Republican Party right now, I think there will be a sense that, you know, everyone should let bygones be bygones right now because it has been quite a rough and tumble primary. But yes, I think that people want to see President Obama's speech, he has done a good job in the past and if he's going to go for by the way and try to sort of push on a lines on comedy a little bit, and he has I think has gotten bigger, as he's done this year after year, this would be the year to see it. So, I am looking forward to see it.

BERMAN: You want him to go for it. You want the President to --

SEXTON: Of course I want him to go for it. President Obama bombs, can't even have a night of joy with everybody. So, I win either way. So, I hope he's, you know, right on the edge.

BERMAN: Kayleigh, do you think Donald Trump should get a response tonight? It's like, you know, it's like this State of the Union with the Republican response. Do you think Donald Trump --

MCENANY: Hey, that would be awesome. I would love to see a Donald Trump rebuttal because I think he could be as funny as the President just like sort of off script. So, I think it would be hysterical. And by the way, it takes the narrative of Ted Cruz right before Indiana. You know, making fun of Donald Trump better than talking about a Carly Fiorina VP. So --

SEXTON: Well, the good news for Ted Cruz though is it's definitely going to be harder than really score those big jokes against Ted Cruz I think --

MCENANY: Oh, I don't know --

HILL: I don't know about that.


MCENANY: I think you have to realize there is a lot of hilarity.

BERMAN: What we're going to do is we're going to take a break and the comedians here are going to come up with their best Ted Cruz jokes. We'll come back and deliver them.

All right. Keep up with all things political, the good, the bad, and the ridiculous. Just download the new CNN politics app. This thing is awesome. It's available in the iTunes store.

We're going to take a quick break. Don't go away. We're standing by for the arrival of the first couple. That's not them, that's Princess Leia.


[19:59:48] BERMAN: It is 8:00 in the East Coast right now. No better place to be on earth than sitting in a studio in New York looking at pictures of Washington, D.C.


Welcome back to CNN's Special Coverage of the annual White House Correspondents Dinner. I'm John Berman. We are expecting President Obama to enter the room at any minute. Elvis in the building, almost. We are told. Already, we've seen some of the biggest names in Hollywood, entertainment and beyond, mixing it up with political figures as well.

Look at the red carpet, the fabulous red carpet. The dinner is set to get under way in a few short moments. We don't have the menu. I'm curious what they're serving. A little later we'll going to take you inside.