Tamra Davis’ comedy movie “Billy Madison” followed the exploits of the eponymous character, played by Adam Sandler.
In the film, Madison is a wealthy but immature 27-year-old man who has to repeat grades 1 through 12 to prove himself worthy of inheriting his father’s Fortune 500 company, Madison Hotels.
Sandler’s supporting cast includes Bradley Whitford, Bridgette Wilson, Darren McGavin, and Norm Macdonald in his movie debut.
“Billy Madison” released on February 10, 1995, meaning it turned 30 last year. Wouldn’t it be nice to see the cast as they are now, compared to how they looked when it hit theaters? Let’s do that now…
Adam Sandler (Billy Madison)
GettyActor, comedian, filmmaker, and singer-songwriter Adam Sandler played the eponymous character in “Billy Madison.” Madison is the wealthy but immature 27-year-old heir to his father’s Fortune 500 hotel chain, and he must return to school to prove he’s worthy of inheriting it.
Age when “Billy Madison” released: 28.
Selected movie credits before “Billy Madison”: Shakes the Clown (1991), Coneheads (1993), Airheads (1994).
Above is a 2026 social media post by Adam Sandler with a couple of recent pictures of him.
Age now: 59.
Selected movie credits after “Billy Madison”: Happy Gilmore (1996), Click (2006), Uncut Gems (2019).
Filmography info per IMDb.
Bradley Whitford (Eric Gordon)
Above is a social media post with a picture of Bradley Whitford (R) with Larry Hankin in Billy Madison.
Actor and producer Bradley Whitford played Eric Gordon in “Billy Madison.” Gordon is the ambitious but conniving Executive Vice President of Madison Hotels who tries to oust Billy from his inheritance.
Age when “Billy Madison” released: 35.
Selected movie credits before “Billy Madison”: Young Guns II (1990), RoboCop 3 (1993), Philadelphia (1993).
GettyAge now: 66.
Selected movie credits after “Billy Madison”: Bicentennial Man (1999), The Cabin in the Woods (2012), Get Out (2017).
Filmography info per IMDb.
Josh Mostel (Principal Max Anderson)
Above is a social media post with several pictures of Josh Mostel, the bottom right of which is one of him in “Billy Madison.”
Stage and screen actor Josh Mostel played Principal Max Anderson in “Billy Madison.” Anderson is the principal of the school the eponymous character goes to, and a former professional wrestler called “the Revolting Blob”, who accidentally killed an opponent in the ring.
Age when “Billy Madison” released: 48.
Selected movie credits before “Billy Madison”: Jesus Christ Superstar (1973), Sophie’s Choice (1982), City Slickers (1991).
Above is a 2025 social media post featuring a picture of Josh Mostel. Recent pictures of Mostel are hard to come by, but despite the date of this one being unspecified, it’s far more recent than 1995 and is estimated to have been taken between 2015 and 2020.
Age now: 79.
Selected movie credits after “Billy Madison”: The Basketball Diaries (1995), Big Daddy (1999), Bad Shabbos (2024).
Filmography info per IMDb.
Bridgette Wilson (Veronica Vaughn)
GettyRetired actress, singer, model and beauty queen Bridgette Wilson — or Bridgette Wilson-Sampras, as she’s now known — played Veronica Vaughn in “Billy Madison.” Veronica is a smart third-grade teacher who teaches the eponymous character and ultimately becomes his love interest.
Age when “Billy Madison” released: 21.
Selected movie credits before “Billy Madison”: Last Action Hero (1993), Higher Learning (1995).
GettyAge now: 52.
Selected movie credits after “Billy Madison”: Mortal Kombat (1995), I Know What You Did Last Summer (1997), House on Haunted Hill (1999).
Filmography info per IMDb.
Norm Macdonald (Frank)
GettyCanadian stand-up comedian, actor, and writer Norm Macdonald played Frank in “Billy Madison.” Frank is the eponymous character’s lazy, pool-lounging friend who supports him during his back-to-school adventure.
Age when “Billy Madison” released: 35.
Selected movie credits before “Billy Madison”: N/A.
GettyAge now: Sadly passed away in 2021 aged 61.
Selected movie credits after “Billy Madison”: The People vs. Larry Flynt (1996), Dr. Dolittle (1998), Vampire Dog (2012).
Filmography info per IMDb.
Darren McGavin (Brian Madison)
GettyVeteran actor Darren McGavin played Brian Madison in “Billy Madison.” Brian is the eponymous character’s father, and owner of a Fortune 500 hotel company who is reluctant to hand over control of it to his immature son.
Age when “Billy Madison” released: 72.
Selected movie credits before “Billy Madison”: Cold Feet (1978), A Christmas Story (1983), Happy Hell Night (1992).
Above is a social media post with a picture of Darren McGavin (R) with Adam Sandler in “Billy Madison.”
Age now: Sadly passed away in 2006 aged 83.
Selected movie credits after “Billy Madison”: Small Time (1996), Pros and Cons (1999), Still Waters Burn (2008).
Filmography info per IMDb.
Larry Hankin (Carl Alphonse)
Above is a social media post with a picture of Larry Hankin in an episode of “Friends” circa 1995.
Character actor Larry Hankin played Carl Alphonse in “Billy Madison.” Carl is is the loyal and trusted operations manager of Madison Hotels who the eponymous character ultimately decides to give control of his father’s company to.
Age when “Billy Madison” released: 57.
Selected movie credits before “Billy Madison”: Annie (1982), Planest, Trains, and Automobiles (1987), Home Alone (1990).
Above is a social media post showing Larry Hankin in 2024.
Age now: 88.
Selected movie credits after “Billy Madison”: Vegas Vacation (1997), Money Talks (1997), El Camino: A Breaking Bad Movie (2019).
Filmography info per IMDb.
“Billy Madison” may not be the greatest comedy movie ever made, but it finds Adam Sandler in joyous form, and its game supporting cast make it well worth a watch.
May Norm Macdonald and Dennis McGavin rest in eternal peace.
