He’s the man of $100 million box office hits. Whether he’s starring in his trademark goofy comedies from his own Happy Madison production company or more ambitious dramedies, Sandler’s been one of the busiest guys in showbiz for years, and one of the most profitable. Here, in time for his latest man-child comedy Grown Ups 2, we take a look at some of the milestones on Sandler’s road to comedy movie superstardom.

Airheads (1994)

Strangely enough, Sandler started off third-string in his first major motion picture, behind early ‘90s star Brendan Fraser and Steve Buscemi. Together, they’re “The Lone Rangers,” a heavy metal group that hijacks a radio station to get more airtime. It’s a sleight film, but one that has lots of cult admirers who enjoy seeing Sandler steal the show as dimwitted rocker Pip.

Billy Madison (1995)

This early Sandler star vehicle features the comedian doing what he does best – acting the man-child part to the hilt. Here, Sandler’s Billy Madison - an heir to his dad’s corporate empire - is forced to prove himself first by re-taking and passing grades 1-12 in 24 weeks.

Happy Gilmore (1996)

Along with Caddyshack, Happy Gilmore is perhaps the greatest golf comedy, and one of Sandler’s most beloved movies. As an unsuccessful hockey player who possesses a powerful swing on the links, Sandler gets to have all kinds of good fun with co-stars Carl Weathers, Christopher McDonald’s “Shooter McGavin” and – in a classic cameo – “The Price Is Right”’s Bob Barker.

The Wedding Singer (1998)

Here’s where Sandler the superstar really broke out, playing a wedding singer from the ‘80s who’s not just loud, but also awfully loveable alongside equally adorable waitress Drew Barrymore. The story’s nothing too original, but the soundtrack is spot-on, and the stars have a sweet chemistry.

The Waterboy (1998)

After the phenomenal success of The Wedding Singer, Sandler scored again in 1998 with the outrageous tale of The Waterboy, a stuttering guy named Bobby Boucher with anger management issues that allow him to transform into a football machine and knock the stuffing out of opposing running backs. Similar to Happy Gilmore, it’s an easy laugher with classic Sandler temper tantrums.

Big Daddy (1999)

Sandler showed some signs of evolvement with this tale of a man-child who actually has to take care of a real child. Of course, the big daddy in question is really posing as the guardian of his buddy’s kid in order to show responsibility and win back his old girlfriend. But those are minor quibbles, right?

Punch-Drunk Love (2002)

The first real “grownup” role for Sandler was this critically acclaimed P.T. Anderson arthouse dramedy. Sandler stars as a small business owner whose chance at love with a shy family acquaintance is threatened by some bizarre circumstances involving a phone sex hotline. It’s dark, tense entertainment – and well worth watching for Sandler’s intense performance.

50 First Dates (2004)

Six years after their initial pairing onscreen, Sandler and Drew Barrymore reunited for more romantic hijinx, this time in Hawaii, where Sandler’s lovestruck veterinarian vies for the hand of Barrymore’s art teacher – a woman with a peculiar form of amnesia where she loses her memory every night.

Spanglish (2004)

Sandler teamed up with filmmaker James L. Brooks (Terms of Endearment) for this drama/comedy about a well-known chef (Sandler), his wife and two kids, and their relationship with their Mexican housekeeper (Paz Vega) and her kids. It’s leagues away from Happy Gilmore, but as with Punch-Drunk Love, Sandler shows he can handle a punchline and straight-ahead dramatic fare.

Reign Over Me (2007)

While some of its post-09/11 themes are more well-meaning than successfully conveyed onscreen, this tale of loss – a story of a man (Sandler) whose family perished on 09/11, and who reconnects to society with the help of his former college roommate (Don Cheadle) – once again showcases Sandler’s ability, and willingness, to stretch his dramatic chops.

You Don’t Mess with the Zohan (2008)

True to his base of admirers who prefer him in more lighthearted projects, Sandler returned to his bread and butter with You Don’t Mess with the Zohan, a movie that recounts the adventures of an ex-Israeli commando known as the Zohan, who journeys to New York to accomplish his lifelong dream of becoming a top hairstylist.

Grown Ups (2010)

Sort of the middle ground between his juvenile comedies and his “adult” fare, Grown Ups found Sandler mixing it up with literal kids and fellow comedy stars Chris Rock, David Spade, Kevin James and Rob Schneider as childhood friends who get together for a raucous Fourth of July weekend – with their respective clans - and fan bases - in tow.

Grown Ups 2 (2013)

The all-star comedy cast from Grown Ups returns (with some new additions) for more summertime laughs. Lenny (Adam Sandler) has relocated his family back to the small town where he and his friends grew up. This time around, the grown ups are the ones learning lessons from their kids. Grab tickets here!