1987: Performing at the Comic Strip

Sandler is a household name today, but in the 1980s, he was one of many comedians and small-time actors. He’s pictured here doing a set at the Comic Strip in New York City, a renowned comedy club where stars like Jerry Seinfeld and Eddie Murphy also got their starts.

1991: 'Saturday Night Live' Kick-Off Party

The comedian was initially hired by Saturday Night Live as a writer in 1990 but joined the cast as a featured player just one year later. Sandler is seen here leaving the show’s annual kick-off party at Rockefeller Plaza in New York City.

1993: With the 'Saturday Night Live' Cast

The star smiles alongside his SNL cast members, including Chris Farley, Mike Myers, Ellen Kleghorne, Rob Schneider, and David Spade. Sandler's SNL stint ended two years later, but his hilarious characters like Opera Man still live on.

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1993: CMJ Music Marathon

Besides acting and comedy, Sandler can also carry a tune—you might be familiar with his singing and guitar playing from his time on SNL. He was snapped here in 1993 performing during the CMJ Music Marathon in New York City.

1994: MTV Video Music Awards

Sandler posed with fellow Hollywood great Sandra Bullock backstage during the 1994 MTV VMAs. This same year, the comedian appeared in Airheads and Mixed Nuts, while Bullock starred in Speed and Who Do I Gotta Kill?.

'Billy Madison' New York City Premiere

A year later, Sandler would make a splash in Billy Madison, where he plays the immature main character who’s forced to redo all twelve grades of school so that he can take over his retiring father’s hotel empire. Sandler’s performance was nominated for an MTV TV + Movie Award and the film remains a cult classic today.

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1996: 'Happy Gilmore' Los Angeles Premiere

Sandler kept the funny movies coming when he released the side-splitting sports comedy Happy Gilmore just one year later. He plays a short-tempered and struggling ice hockey player who suddenly discovers his talent for golf, and enters a tournament to help pay off his grandmother’s debts to the IRS.

1997: Hanging Out at 'Chris Rock Live'

In 1997, Sandler posed with his friends, comedians Chris Farley, Chris Rock, and David Spade, while attending Chris Rock’s comedy show. Sandler shot the excellent rom-com The Wedding Singer later this year.

1997: With Drew Barrymore

Barrymore and Sandler go way back. They’re pictured here in the late ‘90s at a pediatric AIDS benefit in Beverly Hills. The two have starred in a handful of movies together, including The Wedding Singer, 50 First Dates, and Blended.

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1998: Very Casual at LAX

In 1998, Sandler was snapped at LAX wearing a blue and orange Starter jacket, a yellow Pittsburgh Steelers cap, and a graphic tee. Besides The Wedding Singer, Sandler also starred in The Waterboy and Dirty Work that year.

1998: 'The Waterboy' New York City Premiere

Speaking of The Waterboy, the Hollywood star is pictured here at the film’s New York City premiere wearing a zip-up Yankees jacket and a red polo shirt. In the movie, Sandler plays a college football team’s waterboy who is a bit of a punching bag for the team, but joins the roster after they discover he can play. Kathy Bates and Henry Winkler also appear in the film.

1999: 'Big Daddy' Los Angeles Premiere

Sandler made yet another hit with Big Daddy, the funny dramedy about a law school grad who adopts a young boy named Julian to impress his girlfriend. Dylan and Cole Sprouse both played the role of Julian and posed here with Sandler on the red carpet.

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