Natty recently posted 10 classic funny Billy Madison moments, and I was somewhat startled to see how young Adam Sandler looked in those clips. He’s gone from playing a kid, essentially, to playing a comedian toward the end of his career in Apatow’s upcoming Funny People. Sandler has been in the comedy game for a long time now, and he appears to be just as relevant now as he was almost 15 years ago. Say what you want about his newer movies, but Sandler is still a huge draw. Like Paul did with Brad Pitt, I’ve assembled a photo retrospective of Sandler chronicling the major roles in his career. Photos – and aging – after the jump.
Funny People (2009) – George Simmons
I think Funny People will be a lot like Apatow’s last, Knocked Up: a well-written movie with some well-developed characters, a real, sentimental story, and funny parts that are downright hilarious. Sandler is going to have to really act in Funny People, too.
Bedtime Stories (2008) – Skeeter Bronson
I imagine this must have been a fun movie for kids, but it’s the same type of safe crap that Eddie Murphy does. Is this what happens to all comedians when they age? I’m looking at you, too, Steve Martin.
You Don’t Mess With The Zohan (2008) – Zohan Dvir
Many people have told me this movie is terrible – there’s no way it can be worse than The Love Guru – but there was a guy seated in front of me on a plane and watching it. He was absolutely losing his sh*t. I usually find Sandler funny, but I don’t know about this one.
I Know Pronounce You Chuck & Larry (2007) – Chuck Levine
I gave this movie a chance on cable once and it was actually pretty funny.
Reign Over Me (2007) – Charlie Fineman
Sandler goes for the Bob Dylan look here. A drugged-up, homeless Dylan.
Click (2006) – Michael Newman
Click seems worse than Bedtime Stories; it’s the type of idea you’d come up with if you were making a joke about a hypothetical Adam Sandler movie.
The Longest Yard (2005) – Paul Crewe
I thought Sandler actually looked pretty good throwing the football in The Longest Yard. If memory serves me correctly, Sean Salisbury coached him before and during filming.
Spanglish (2004) – John Clasky
I love the hair helmet.
50 First Dates (2004) – Henry Roth
Sandler definitely comes across as very charming. He’s not the best-looking guy, but I can certainly see why lots of girls find him very attractive.
Anger Management (2003) – Dave Buznik
A photo retrospective of Jack Nicholson would be kind of cool to see. It would also take forever to compile.
Mr. Deeds (2002) – Longfellow Deeds
I love Sandler’s rendition of Space Oddity in this movie. However, I think this is right about the time Sandler went from making really funny movies to moderately funny movies.
Punch-Drunk Love (2002) – Barry Egan
I never saw this, but I’ve always been intrigued by the Sandler-Paul Thomas Anderson pairing. How is this flick? I think I want to give it a try.
Little Nicky (2000) – Nicky
I promise, this movie does get funnier after multiple viewings. That’s not to say that it’s real funny, though. Sandler’s friends are actually funnier than he is in Little Nicky.
Big Daddy (1999) – Sonny Koufax
This movie had the perfect mix of “cuteness” and comedy. Sandler interacting with kids is usually pretty funny.
The Waterboy (1998) – Robert “Bobby” Boucher, Jr.
The Waterboy is a pretty underrated Sandler comedy. It’s nowhere near the level of Happy Gilmore or Billy Madison, but it’s pretty rewatchable, and some of the hits never seem to get old.
The Wedding Singer (1998) – Robbie
I think this may be the first movie where Sandler showed his sensitive side and actually acted a bit. He didn’t play a complete buffoon in this one.
Bulletproof (1996) – Moses
I actually saw this movie, but it didn’t work for me. Not because Sandler isn’t funny, but because Damon Wayans is wasted as the straight man.
Happy Gilmore (1996) – Happy Gilmore
Happy Gimore is a classic, and Shooter McGavin is one of the best comedic villains ever. A very, very strong follow up to Billy Madison.
Billy Madison (1995) – Billy Madison
Quite simply one of the funniest comedies ever. I will not argue this.
Mixed Nuts (1994) – Louie
Before Sandler’s more well-known roles, he was part of an intewresting ensemble cast in Mixed Nuts.
Airheads (1994) – Pip
Airheads isn’t bad. I feel like it’s on Comedy Central at least once every two weeks.
Saturday Night Live (1990-1995) – Himself
Sandler did so many great things on SNL: Canteen Boy, all his songs and appearances on Weekend Update, The Herlihy Boy, and so on. I don’t know that SNL will ever be as good as it was in the early 90s.
Going Overboard (1989) – Schecky Moskowitz
I’m pretty sure this is considered one of the worst movies ever made. It’s got to have at least one or two funny parts, though, right?
The Cosby Show (1987-1988) – Smitty
Sandler was hanging with Theo Huxtable before anyone knew who he was.