But as the Briton will be all too aware, the great Brazilian is streets ahead -- six victories compared to just one -- at the Monaco Grand Prix.
It was on the principality's winding roads -- widely considered the sport's most technically challenging circuit -- where Senna routinely showcased the genius that so enthralled Hamilton when he was growing up.
"Ayrton was sitting in the car shifting and turning, looking like he was on the edge, which he obviously was. I was like, 'I wanna do that, I can do that' -- that's where it started," Hamilton told CNN's The Circuit
It was in 1993 -- the same year of Senna's sixth Monaco triumph -- that an eight-year-old Hamilton first started karting. Before then, he was dreaming of two wheels, not four.
"Motorbikes were what I actually wanted to do before I started racing cars ... I wanted to do dirt bikes, that's what I loved," he explains.
"I am grateful that my dad didn't let me motorbike -- F1 is a much better job to do (and) a bigger sport."
Hamilton is arguably now the biggest name in F1, who, when he's not in the cockpit of his Mercedes, can often be seen mixing with celebrities from music, film and fashion in the United States.
An admirer of how America makes such a spectacle of their sports
, Hamilton doesn't rule out lining up on a grid stateside in the future.
"I like NASCAR. I probably would do a couple of races in NASCAR at some stage at my career," he says.
"I wish that times would not exactly be how they are in the sense that, John Surtees
(the Briton who raced in both F1 and motorcycle world championships) was able to do several different races, different sports ... there's no reason why I can't do a NASCAR race and then come back and do F1 — I would love to be able to do that in the mid part of the season."
For now though, the focus is on F1 and notching a second win at Monaco.
Last year was perhaps his most frustrating failure yet — a miscalculation by his Mercedes team saw Hamilton squander the lead late in the race, handing victory to his teammate and arch rival Nico Rosberg.
A misfiring start to the 2016 season — Hamilton is winless so far — and a calamitous collision with Rosberg at the Spanish Grand Prix, have raised the stakes in Monaco to unprecedented new heights.
A win this weekend would revive a stalling title challenge, helping claw back a 43-point deficit
Championship points aside, Hamilton doesn't really want for much else these days -- apart from maybe one thing.
"Right now, I wish could have some pancakes but I can't have pancakes because I've gotta be a certain weight, but otherwise, no," he says.
"Along the way there is a lot of sacrifices that you and your family goes through ... you just have to find the right balance. Ultimately, winning the championship and succeeding is what you want to do most.
"I don't know who said it but, winning a gold medal or winning a championship or winning a race is a great thing but if you are not enough without it, you will never be enough with it.
"So it's all about trying to make sure you're enjoying, you're growing outside because that uplifts you when you do succeed."