Not only does the man have two Oscar nominations under his belt but 14 of the last 19 films he’s starred in have individually earned over $100 million at the box office worldwide. It seems that however you define success, Will Smith is killing it and with a slew of sequels in development he doesn’t seem to be slowing down anytime soon. In lieu of his new film Men In Black 3 releasing this month, I decided to take a look at Smith’s 5 best roles.

#5. TIE - Mike Lowery in Bad Boys  / Captain Steven Hiller in Independence Day – Ok so I know I am totally cheating here! Two roles for one spot on the list? Yes and I’m doing it because it’s my list and I have my reasons. Both characters are supremely familiar to even the average movie-goer: one is a wise cracking cop, the other a wise cracking Marine pilot (see, they’re not so different!) And even though a lot of Smith’s character’s fall into this category, there is something special about the way he connects audiences to his roles. Even if his characters can be categorized as safe or even corny, Will can set himself apart because he is both genuinely funny and likable. That “it” factor has been an undeniable asset to him throughout his career.

#4. Jay in Men in Black – Similar to those tied roles at the number five spot, I bumped up his character Jay from Men In Black because as much as I love Bad Boys (and Bad Boys 2 for that matter) I think this is Smith’s funniest role. It also manages to be probably the most fun film as well. Will’s brand of energetic smooth talk fits magnificently alongside super serious Tommy Lee Jones (as Kay.) The two build a match made in sci-fi comedy heaven and Smith’s character delivers some funny lines I still quote to this day.

#3. Muhammad Ali in Ali – You can’t have a ‘best roles’ list and not mention the performance that earned Will Smith his first Oscar nomination. He spent many months researching Ali’s real life, undertaking extensive boxing training and gaining a considerable amount of weight for the role. Although the film received mixed to positive reviews, the performances of the movie, chiefly Smith’s, were almost universally praised.

#.2 Chris Gardner in The Pursuit of Happyness – Annnd here comes Oscar nom number two! Although I’m not a fan of the factual liberties taken with the story of the real dude the film was based on, Smith gives an undeniably moving performance. Maybe the fact that he was acting alongside his real life son made the chemistry really resonate onscreen, but whatever it is, his performance is the real overwhelming reason to watch the film.

#1. Paul in Six Degrees of Separation – A possible surprise to some, but the enigmatic Paul from Six Degrees comes to the top of my list for good reason. Firstly, it’s a role that is quite different than most of the actor’s filmography but one that still manages to put his likable nature to great use. Paul is a cultured and charming young man that finds his way into the tight-knit fabric of a privileged Manhattan family. He seems to be an exceptional gentlemen meshing glouriously with the entire family, but Paul is not what he seems. Along with a stunning turn from Stockard Channing (who received a Best Actress nom,) Will gives us a performance that will keep you glued to his character from the first scene.

What do you think about Will Smith? What roles do you think are his best?