From The Waterboy to His Wedding Day, the Most ’90s Photos of Adam Sandler

The actor has been bringing the laughs for almost four decades

Adam Sandler at the Four Seasons Hotel, January 9, 1998 in Beverly Hills, California.

A young Adam Sandler in 1998. PHOTO: GETTY IMAGES/BOB RIHA, JR.

So many artists helped define the 1990s, but Adam Sandler definitely sits high on that list.

The actor and comedian has been working in the industry since the late 1980s, though the ’90s delivered some of his incredibly memorable bits from SNL, not to mention a string of blockbuster movies including Happy Gilmore, The Wedding Singer, The Waterboy and Billy Madison.

Here, check out some oh-so-’90s throwbacks of a young Adam Sandler promoting some of his biggest projects (so far!).

01of 15

That Rocks

Adam Sandler during 1995 MTV Rock the Vote in Los Angeles, California, United States.

A young Adam Sandler.JEFF KRAVITZ/FILMMAGIC

At 29 years old, Adam Sandler hit up the 1995 MTV Rock the Vote event in L.A.

02of 15

Guitar Hero

Musical guest Adam Sandler performs on June 5, 1996

A young Adam Sandler on ‘SNL’.MARGARET C. NORTON/NBCU PHOTO BANK/NBCUNIVERSAL VIA GETTY

On a 1996 episode of The Tonight Show, Adam Sandler brought along his trusty guitar for a performance.

03of 15

Smooth Ride

Adam Sandler during "Happy Gilmore" Premiere at Cineplex Odeon Century Plaza Cinema in Century City, California, United States.

A young Adam Sandler.SGRANITZ/WIREIMAGE

Appropriately, Adam Sandler drove a golf cart to the 1996 premiere of Happy Gilmore.

04of 15

Perfect Pairing

Actress Drew Barrymore and comedian Adam Sandler attend "The Wedding Singer" Memorabilias Donated to Planet Hollywood on February 5, 1998 at Planet Hollywood in New York City.

A young Adam Sandler and Drew Barrymore.RON GALELLA, LTD./RON GALELLA COLLECTION VIA GETTY

In one of the most ’90s moments ever, Adam Sandler and The Wedding Singer costar Drew Barrymore donated items from their film to Planet Hollywood in New York City in 1998.

05of 15

Desk Job

Dennis Miller, Adam Sandler during 'Weekend Update' on April 20, 1991

A young Adam Sandler on ‘SNL’.ALAN SINGER/NBC/NBCU PHOTO BANK

In one of his first years on SNL, Adam Sandler hit the “Weekend Update” desk as a smiling Dennis Miller looked on.

06of 15

Suit Yourselves

10/6/98 New York City Adam Sandler With Co-Star Cole Sprouse Filming "Big Daddy" In Nyc

A young Adam Sandler and Cole Sprouse.ARNALDO MAGNANI/GETTY

At the 1998 premiere of Big Daddy, Adam Sandler twinned with his pint-size costar, a young Cole Sprouse.

07of 15

In Bloom

Adam Sandler at the Four Seasons Hotel, January 9, 1998 in Beverly Hills, California.

A young Adam Sandler.GETTY IMAGES/BOB RIHA, JR.

Adam Sandler was smelling the flowers at the Four Seasons Hotel in Beverly Hills in January of 1998.

08of 15

Triple Threat

Adam Sandler, Will Ferrell, and Mike Myers

A young Adam Sandler, Will Ferrell and Mike Myers.THEO WARGO/WIREIMAGE

Were we ever so young? Adam Sandler, Will Ferrell and Mike Myers looked ageless backstage at Madison Square Garden in October of 2001 for The Concert for New York City.

09of 15

Sing Thing

Adam Sandler sings during "Weekend Update" on May 13, 1995

A young Adam Sandler on ‘SNL’.AL LEVINE/NBCU PHOTO BANK/NBCUNIVERSAL VIA GETTY

In his years on SNL, Adam Sandler often integrated song, like in this “Weekend Update” Mother’s Day sketch.

10of 15

Four of a Kind

Chris Farley, Chris Rock, Adam Sandler & David Spade

A young Adam Sandler with Chris Farley, Chris Rock and David Spade.JEFF KRAVITZ/FILMMAGIC

Name a more iconic quartet! Adam Sandler hung with hilarious friends Chris Farley, Chris Rock and David Spade in this undated snap.

11of 15

To a T

Adam Sandler during Mr. Deeds Premiere at Loews Lincoln Square in New York City, New York, United States.

A young Adam Sandler.JIM SPELLMAN/WIREIMAGE

Adam Sandler showed his FDNY pride for the 2002 premiere of Mr. Deeds in New York City.

12of 15

Tux Time

Adam Sandler during Kid's Choice Awards Backstage in Santa Monica, California, United States.

A young Adam Sandler.JEFF KRAVITZ/FILMMAGIC

The actor tuxed up in 2002 for the 15th Nickelodeon Kids Choice Awards in L.A.

13of 15

They Do

 Adam Sandler poses with his bride model-actress Jackie Titone at their wedding June 22, 2003 in Malibu, California.

Adam Sandler and wife Jackie on their wedding day.NICK GOSSEN/COURTESY OF ADAMSANDLER.COM/GETTY

It’s not a movie still! Adam Sandler and wife Jackie looked picture-perfect on their June 2003 wedding day in Malibu.

14of 15

Flower Power

Adam Sandler during "50 First Dates" Premiere at Mann Village Theatre in Westwood, California, United States.

A young Adam Sandler.SGRANITZ/WIREIMAGE

The star brought the vibes for the 2004 L.A. premiere of his rom-com, 50 First Dates.

15of 15

Total Baller

Adam Sandler during Chris Rock and Adam Sandler Visit BET's "106 & Park" - May 26, 2005 at BET Studios in New York City, New York, United States.

A young Adam Sandler.JOHN RICARD/FILMMAGIC

Adam Sandler sported his signature style on a visit to BET’s 106 & Park with pal Chris Rock (not pictured) in 2005.

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