'Billy Madison': Grab Your Backpack, Head Back to School and Catch Up with the Cast 29 Years Later

It's time to go back to school with Adam Sandler, Chris Farley and the rest of the Billy Madison cast. And while the movie first hit theaters in 1995, we decided to celebrate its 29th anniversary rather than its 30th, because ... well, why not?

The film follows Billy Madison (Adam Sandler) as he goes back to school to undergo an accelerated grades kindergarten through 12 in an effort to earn his high school diploma so that he can take over his father's multi-million dollar hotel franchise before his arch enemy can.

Billy Madison, which earned $26.4 million at the box office, is currently available for streaming on Amazon Prime Video.

Adam Sandler: Billy Madison cast

CHARACTER PLAYED: Billy Madison

BORN: September 9, 1966 in Brooklyn, New York.

BEST KNOWN FOR: Saturday Night Live (1970-1995), Happy Gilmore (1996), The Waterboy (1998), 50 First Dates (2004), Grown Ups (2010), Just Go with It (2011), Uncut Gems (2019) and Spaceman (2024).

PERSONAL: Sandler has been married to Jackie Sandler since 2003. They have three children together

THOUGHTS ON BILLY MADISON: "When Billy Madison came out, me and my friend who wrote it, we were just, like, 'Oh yeah, they're going to write about this in New York!' We grew up reading the papers, we were going to NYU. And then we read the first one [review] and we were, like, 'Oh my god, what happened? They hate us.' And then we were, like, 'It must have been this paper,' but then 90 percent of the papers are going 'This is garbage.'"

FUN FACT: While filming, Sandler actually hit kids with dodgeballs during the game, causing a lot of kids to cry.

Darren McGavin

CHARACTER PLAYED: Brian Madison

BORN: May 7, 1922 in Spokane, Washington.

DIED: February 25, 2006 at age 83.

BEST KNOWN FOR: Crime Photographer (1951-1952), The Man with the Golden Arm (1955), Mike Hammer (1958-1959), Riverboat (1959-1961), Kolchak: The Night Stalker (1974-1975), A Christmas Story (1983), Raw Deal (1986) and Still Waters Burn (2008).

PERSONAL: McGavin was married to Melanie York from 1944 to 1969, and they had four children together. Then he married Kathie Browne later that same year and remained with her until her death in 2003.

FUN FACT: Dustin Hoffman, Richard Dreyfuss and Jack Nicholson were also considered for the role of Brian.

Bridgette Wilson-Sampras: Billy Madison cast

CHARACTER PLAYED: Veronica Vaughn

BORN: Gold Beach, Oregon, on September 25, 1973.

BEST KNOWN FOR: Santa Barbara (1992-1993), Last Action Hero (1993), I Know What You Did last Summer (1997), The Wedding Planner (2001), The $Street (2000-2001) and Phantom Punch (2008).

PERSONAL: Wilson-Sampras has been married to Pete Sampras. They have two children together. Currently the actress is battling ovarian cancer, with her husband saying, "Last December, my wife, Bridgette, was diagnosed with ovarian cancer. Since then, she has had major surgery, pushed through chemotherapy and continues with targeted maintenance therapy. It is hard to watch someone you love go through a challenge like this. However, seeing our boys step up and be such strong supporters of Bridgette, myself and each other has been amazing. Watching Bridgette continue to be an incredible mom and wife through it all has been inspiring."

FUN FACT: Wilson-Sampras was only 20 years old during filming.

Bradley Whitford

CHARACTER PLAYED: Eric Gordon

BORN: October 10, 1959 in Madison, Wisconsin.

BEST KNOWN FOR: Adventures in Babysitting (1987), The West Wing (1999-2006), The Cabin in the Woods (2011), Savings Mr. Banks (2013), Get Out (2017), The Darkest Minds (2018), The Handmaid's Tale (2018-2022) and Parish (2024).

PERSONAL: Whitford was married to Jane Kaczmarek from 1992 to 2010, and they had three children together.  Then he married Amy Landecker in 2019 and they have been together ever since.

THOUGHTS ON BILLY MADISON: Whitford only got the part of Eric Gordon when actor Philip Seymour Hoffman said no. Adam Sandler remembers: “I was in Toronto getting ready to make the movie and it wasn’t cast yet and I saw Philip Seymour Hoffman's [audition] and I was laughing my -ss off. I’m, like, ‘Who is this guy?!? He’s hilarious!' Then we offered it to him, and we get this call back, ‘Yeah, like, he doesn’t wanna do it.’ And we were like, ‘He doesn’t wanna do it? What do you mean, he auditioned!" It worked out well for Whitford, though, since he won the role instead.

FUN FACT: Whitford's character was supposed to be arrested at the end of the film, but Sandler changed it.

Chris Farley: Billy Madison cast

CHARACTER PLAYED: Bus Driver

BORN: February 15, 1964, in Madison, Wisconsin.

DIED: December 18, 1997 at age 33.

BEST KNOWN FOR: Tommy Boy (1995), Black Sheep (1996), Saturday Night Live (1990-1996) and Almost Heroes (1998).

PERSONAL: His real name is Christopher Crosby Farley.

THOUGHTS ON BILLY MADISON: Farley died two years after the movie came out and to this day Sandler still pays tribute to him by singing the "Chris Farley Song" on stage whenever he gets the chance. "I've sang it maybe a hundred times already, but it rocks me. I think it's 'cause we show video of Chris, and I see his face, and I remember his dad and I'm friends with his brothers, his mom, and everybody and they still miss him a lot. It gets me,"  Sandler revealed on the Happy Sad Confused podcast.

FUN FACT: Farley drank six cups of espresso before shooting the school bus scene to try and get that angry energy.

Larry Hankin

CHARACTER PLAYED: Carl Alphonse

BORN: December 7, 1937 in New York City, New York.

BEST KNOWN FOR: Solly's Diner (1980), Pretty Woman (1990), Home Alone (1990), Friends (1994-1996), The Wager (2004), The Alphabet Killer (2008) and The Invisible Raptor (2023).

PERSONAL: Hankin has a degree in industrial design from the University of Syracuse.

THOUGHTS ON BILLY MADISON: In the film Hankins makes a mousey face, and recalled on the Beyond the Backlot podcast that was what won him the part. Hankin one day met Adam Sandler for lunch and asked him if he could make a funny face. Hankin replied, "'I do it for little children, but I don't want to do it for you'. So he [Sandler] goes, 'No, no, do it.'  And one of the things about Adam is he's pretty insistent and he can get you to do anything. So I did this, you know, mouse face, which I ended up doing in the movie."

FUN FACT: Hankin reportedly hated this film, thinking it was too immature.