Where Are They Now? The Cast Of Billy Madison

If you subscribe to Netflix, Adam Sandler’s two Netflix-exclusive movies, The Ridiculous 6 and The Do-Over, are probably being recommended to you after every single thing you watch. Compared to The Ridiculous 6’s historic Rotten Tomatoes score of 0% (The Do-Over fares slightly better with 7%), Sandler’s early films are looking more and more like masterpieces: Billy Madison has a comparatively respectable 46% on Rotten Tomatoes and was named Sandler’s best movie by Rolling Stone last year.

Released back in 1995, Billy Madison was the first film that Sandler carried on his own. Twenty-one years later, a few of the actors have gone on to become superstars, others have quit the business, and several have sadly passed away. Here’s what a Billy Madison class reunion would look like:

14 Steve Buscemi — Danny McGrath

Buscemi was already well-known when he appeared in Billy Madison; now, he’s appeared in over 100 films, from indies to blockbusters, in every genre you can think of. There’s the Coen brothers’ movies, including Barton Fink, Fargo, and The Big Lebowski; children’s movies including Spy Kids 2 and Monsters Inc; classics like Reservoir Dogs, Pulp Fiction and Ghost World; and everything else you can think of. Buscemi rejoined Sandler for a number of movies, including the Hotel Transylvania movies, Big Daddy, Mr. Deeds, the Grown Ups movies and, recently, The Ridiculous 6. He has also directed a number of films, including Lonesome Jim and Interview.

Lastley, Buscemi is hitting a new career high. He won a Golden Globe for his performance in the series Boardwalk Empire, and his recurring role on Portlandia is a hit. He hosts his own Emmy-nominated webseries, Park Bench with Steve Buscemi, and appears with Louis CK in another webseries, Horace and Pete.

13 Darren McGavin — Brian Madison

McGavin made a career out of playing “the dad”: Along with playing Sandler’s dad in Billy Madison, he’s best known for playing the father in The Christmas Story and Murphy Brown (for which he won an Emmy). McGavin’s career spanned over fifty years: He made his film debut in 1945’s A Song To Remember, became a television star in the ‘50s and ‘60s, and found time to act onstage as well.

Sadly, Billy Madison was one of McGavin’s last films. He continued working through the ‘90s, appearing in movies including Pros and Cons and Small Time and some TV series, including The X-Files. He passed away in 2006 at the age of 83, of cardiovascular disease.

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11 Bridgette Wilson — Veronica Vaughn

A former beauty queen, Wilson continued playing “the hot girl” in films throughout the ‘90s and early 2000s. She worked with Sandler again in The Wedding Singer, and also appeared in I Know What You Did Last Summer, House On The Haunted Hill and Shopgirl. Wilson also briefly dabbled in music, releasing two albums in the ‘90s and a country single in 2002. Her most recent film was the 2008 Sonny Liston biopic, Phantom Punch.

Wilson may now be best known for her personal life: She married tennis pro Pete Sampras in 2000, and they have two children. In 2014, the couple made headlines for buying a $6 million Bel-Air mansion. Not bad for a teacher’s salary!

10 Bradley Whitford — Eric Gordon

Whitford has gone on to become an award-winning dramatic actor: He was nominated for three Emmys (winning once) and three Golden Globes for his role in The West Wing, and last year won a second Emmy for his role in Transparent. He’s also keeping up his comedic side, with roles in Happyish, Brooklyn Nine-Nine and Trophy Wife.

Other post-Billy Madison career highlights include Studio 60 On Sunset Strip, The Good Guys and The Mentalist; he’s also appeared in movies including Kate & Leopold, The Sisterhood of the Traveling Pants and Cabin In The Woods. As if that wasn’t enough, Whitford has also dabbled in journalism, writing a column for the Huffington Post, and is an outspoken and politically active Democrat.

9 Josh Mostel — Principal Max Anderson

Mostel is the son of actor Zero Mostel and actress Kathryn Celia. He began his career as a child, singing as a boy soprano in the Metropolitan Opera. Mostel began acting on Broadway in the early ‘70s and soon transitioned to film, appearing in classics like Jesus Christ Superstar and Sophie’s Choice.

Some of Mostel’s post-Billy Madison films include The Basketball Diaries, Rounders, Great Expectations and State of Play. He also worked with Sandler again, in 1999’s Big Daddy. At age 69, he’s still going strong: He last appeared in the drama The Congressman earlier this year.

8 Norm Macdonald — Frank

Norm Macdonald worked with Sandler on SNL, and Billy Madison was just the beginning of their collaboration. They also both appeared in Dirty Work, The Animal, Grown Ups, Funny People, Jack and Jill and The Ridiculous 6. Macdonald also appeared in the Deuce Bigalow movies, which Sandler produced.

Some of Macdonald’s non-Sandler movies include Man on the Moon and Screwed. He’s appeared in TV series including NewsRadio, The Norm Show, My Name Is Earl and The Middle. He’s also an accomplished voice actor: You might recognize his voice from the Dr. Doolittle movies, Family Guy, The Fairly Oddparents and Vampire Dog.

7 Mark Beltzman — Jack

Beltzman has been acting for over 30 years, but still doesn’t have a Wikipedia page! He joined Sandler again in The Wedding Singer. Some of his more memorable roles, in Home Alone and Mo’ Money, pre-date Billy Madison, but he’s kept busy.

Beltzman’s post-Billy Madison highlights include roles in the movies in Lovely & Amazing and Employee Of The Month. He has had recurring roles in the TV series According To Jim, You’ll Be Fine and the Funny Or Die web series The Box’s Edge. He last appeared in a TV movie called The Homeless Detective — joining his Billy Madison costar Larry Hankin.

6 Larry Hankin — Carl Alphonse

Hankin’s career predated Billy Madison by decades: His first big break was in the 1979 movie Escape from Alcatraz and he’s known for appearing in various John Hughes movies, including Planes, Trains and Automobiles, She’s Having A Baby and Home Alone.

Hankin may now be best known for playing Old Joe on Breaking Bad. Other post-Billy Madison career highlights include recurring roles in Friends, Claude’s Crib and The Last Hand and appearances in movies, including Money Talks, Nobel Son and The Alphabet Killer. His recent projects include the TV movie The Homeless Detective, which he also wrote and produced, and the webseries Bad Internet.

5 Robert Smigel — Mr. Oblaski

Along with acting, Smigel is a comedy writer (he got his start on SNL, where he first worked with Sandler, and still writes for the series), comedian, puppeteer and voice actor. He worked with Sandler many times after Billy Madison, appearing in You Don’t Mess With The Zohan, Punch-Drunk Love, I Now Pronounce You Chuck And Larry, Pixels, The Do-Over and Little Nicky and cowriting The Wedding Singer, Little Nicky, the Hotel Transylvania films and You Don’t Mess With The Zohan. 

Outside of his work with Sandler, Smigel is also known for creating and voicing Triumph, The Insult Dog, which debuted in 1997 and became a late ‘90s/2000s talk show and awards show staple — and recently appeared in a Funny or Die election sketch. Smigel’s other recent projects include a guest role in Portlandia and voice acting on Bob’s Burger’s.

4 Jim Downey — Principal

Like Smigel, Downey was a longtime SNL writer, contributing on and off from 1977 through 2013; he also appeared in over 40 SNL sketches, including, memorably, “Andy’s Dad” with Andy Samberg and Jonah Hill.

Downey’s career has focused more on writing than on acting, but he’s not averse to the occasional acting gig. Downey joined Sandler once again for the movie Dirty Work, and also appeared in There Will Be Blood, Curb Your Enthusiasm and 30 Rock, but Billy Madison probably remains his best-known movie as an actor. Downey retired from SNL in 2013 and has kept a low profile since then, though he appeared in the 2015 SNL documentary Live From New York!

3 Theresa Merritt — Juanita

You wouldn’t know it from her role in Billy Madison, but Merritt was a Tony-nominated stage, film and TV actress. Her notable roles include the play Ma Rainey’s Black Bottom, both the stage and film versions of The Wiz, the sitcom That’s My Mama and the movies The Goodbye Girl and Best Little Whorehouse In Texas.

Sadly, Merritt’s career after Billy Madison was short: she appeared in the movies Dangerous Proposition and Home Fries, both in 1998, as well as several TV series. She died in June 1998 at the age of 75, of skin cancer.

2 Chris Farley — Angry Bus Driver

Before his Billy Madison appearance, Farley had acted with Sandler in Airheads, Coneheads, and, of course, SNL. After Billy Madison, Farley starred in Tommy Boy, Black Sheep, Beverly Hills Ninja and Almost Heroes. He reunited with Sandler for a brief appearance in Dirty Work: It was to be his final film.

Farley died in December 1997 at the age of 33, of a drug overdose. He sought treatment for drug abuse and obesity 17 times, but it wasn’t enough. His legacy lives on: He was awarded a star on the Hollywood Walk of Fame in 2005, a biography called The Chris Farley Show was released in 2008, and a documentary, I Am Chris Farley, was released in 2015. Adam Sandler appeared to pay tribute, as did Lorne Michaels, David Spade and many other SNL alumni.

1 Adam Sandler as Billy Madison

Sandler’s comedic sensibility hasn’t changed much in the two decades since Billy Madison, but the formula works for him. Despite constant critical pans, his films continue to rake in the box office dough — they’ve grossed almost $5 billion worldwide. Sandler just released the second film, The Do-Over, in his four-film deal with Netflix — the first, The Ridiculous 6, has been seen more than any other movie in Netflix history, despite historically low critical ratings and accusations of racism against its Native American cast, who walked off the set.

Sandler has released over 40 films since Billy Madison — highlights include The Wedding Singer, Punch-Drunk Love and Funny People. He formed his own production company, Happy Madison Productions (named for Billy Madison and Happy Gilmore, of course), in 1999, and has produced both his own films as well as others, such as Paul Blart: Mall Cop and its sequel. In 2014, Sandler appeared in the documentary I Am Chris Farley to pay tribute to his late Billy Madison co-star.

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Can you think of any other Billy Madison actors who should have been mentioned? Let us know in the comments below!