32 Actors That Were Way Too Old To Be Playing Teens But Did It Anyway

The entertainment industry is a funny place, one with its own set of rules. And one that has happened countless times over the years is that oftentimes the actors playing teenagers are a little long in the tooth to be doing so. Some of these performances are beloved, and others are infamous. There are particularly 32 actors that were way too old to be playing teens but did it anyway. And if you ask me, each performance on this list is pretty iconic.

Working with actual teenagers is tricky, unless the actor is emancipated and able to deal with the long hours usually required for TV and film work. So it's definitely understandable that production have chosen actors who were too long in the tooth to play their respective roles. In no particular order, here are the infamous 32.

Rachel McAdams, Mean Girls

You can't think of Rachel McAdams without her performance as Regina George in Mean Girls. While the cast of Mean Girls was mostly age appropriate, McAdams was actually 25 years old when playing the queen of the plastics. Still, I can't imagine anyone who could have played her better.

Joseph Quinn, Stranger Things

The fourth season of Stranger Things was a star-making moment for Joseph Quinn, who played Eddie Munson. He quickly became a fan favorite, but those same fans might be surprised to learn that he's actually already 29 years old. Unfortunately, the finale of Stranger Things 4 seemingly implied we won't be seeing him again for the final batch of episodes.

Stacey Dash, Clueless

There are a number of epic teen movies on this list, and Clueless is truly a piece of '90s film history. The comedy followed a group of ultra rich high school students, but it turns out that Dionne actress Stacey Dash was 28 when filming her performance in the movie. Plus, she went on to reprise that role in the TV spinoff.

Leonardo DiCaprio, Catch Me If You Can

Steven Spielberg's Catch Me if You Can came out in 2002, and told a true story about an infamous con man, Frank Abagnale Jr.. That was played by none other than Leonardo DiCaprio, and spanned many years of his life, starting at just 17 years old. However, the Titanic actor was actually 28 when he filmed this classic movie.

Alan Ruck, Ferris Bueller's Day Off

John Hughes' Ferris Bueller's Day Off is a classic comedy, one that remains a quotable part of the pop culture lexicon to this day. Succession actor Alan Ruck gave an outstanding performance as Cameron Frye, but he was actually nearly 30 when portraying a high school student opposite Matthew Broderick.

Stockard Channing, Grease

Grease is a beloved movie musical, one that I actually think improves upon the stage musical of the same name. While it's full of iconic performances, a lot of of the cast is  a bit too old for their roles. That includes Rizzo actress Stockard Channing, who was 33 years old. Regardless, she is THE Betty Rizzo, and she absolutely crushed the role.

Shirley Henderson, Harry Potter

The cast of Harry Potter grew up before our eyes, with the kids joined by some legendary actors playing the universe's adults. But fans might not realize that Moaning Myrtle actress Shirley Henderson was actually a 36-year-old adult when portraying the ghostly teenager.

Henry Winkler, Happy Days

Happy Days influenced a lot of pop culture, including being responsible for the term "jumping the shark." Henry Winkler has had a long career since then, but he'll always be Fonzie. Although he wasn't quite a teenager, as he was 28 when he landed that leather-clad role.

Ncuti Gatwa, Sex Education

Sex Education was a beloved teenage comedy for those with a Netflix subscription, and it wrapped up after four seasons. Ncuti Gatwa played fan favorite Eric Effiong, but he was actually 26 when the show first came out.

Andrew Garfield, The Amazing Spider-Man

While Tom Holland was praised for being an authentically young actor in the MCU, his predecessors were a bit older during their run as the wall crawler. Oscar nominee Andrew Garfield was actually 27 when he debuted in The Amazing Spider-Man, portraying playing high school student Peter Parker. And Garfield got to reprise his role in Spider-Man: No Way Home.

Jason Earles, Hannah Montana

Hannah Montana ran for a long time on Disney Channel, and made Miley Cyrus into a megastar. The show also starred Jason Earles as her older brother Jackson. But while he was playing a 16-year-old, he was actually 29 when the show began.

Gabrielle Carteris, Beverly Hills, 90210

Beverly Hills, 90210 has a long run on TV, and is quintessential '90s culture. While some of Beverly Hills, 90210's cast was quite young, Andrea Zuckerman actress Gabrielle Carteris was actually 29 when the show first began.

Keiko Agena, Gilmore Girls

Gilmore Girls is a show that still has a strong fanbase, who re-watch its even season run as well as the Netflix spinoff A Year in the Life. While Alexis Bledel grew up and became a grown actress before our eyes, Rory's best friend Lane was played by Keiko Agena, who was 27 when the show first began.

Ben Platt, Dear Evan Hansen

This entry is one that folks might have guessed would appear. In 2021, Tony winner Ben Platt reprised his role as the title character the Dear Evan Hansen movie. Platt caught a ton of flak for starring in Dear Evan Hansen at 27 years old, and was made into countless memes as a result. Still, I thought he was great in the role and a lot of backlash was unjust; I mean, look at the other entries in this list!

Nicholas Brendan, Buffy the Vampire Slayer

Buffy the Vampire Slayer is a cult classic TV show that's still super popular today. The first three seasons were set at Sunnydale High School, with the characters' personal drama mirroring their battle with demons. But Xander actor Nicholas Brendan was actually 25 when he landed the role in Joss Whedon's TV series.

Johnny Depp, 21 Jump Street

Johnny Depp has had a long career, including a number of truly beloved roles like Edward Scissorhands and Captain Jack Sparrow. But his first big role was as Officer Thomas "Tom" Hanson Jr. in 21 Jump Street. He played a young looking cop posing as a high school student, but was actually 24 years old when he started filming Season 1. And that show would go on to run for 5 seasons.

Paul Rudd, Wet Hot American Summer

Wet Hot American Summer is a cult classic comedy, and follows a group of teen camp counselors who are into all sorts of campy debauchery. Paul Rudd gave a hilarious performance as Andy, but was actually 31 years old. Although that's nothing since the cast of Wet Hot American Summer reprised their roles in a Netflix show, all of whom were vastly over the age of their characters.

Gabrielle Union, Bring It On

Bring It On is another beloved teen movie, one that centers around two rivaling high school cheer squads in California. Gabrielle Union gave a killer performance as Isis, although she was actually 27 at the point of filming.

Audrey Hepburn, Breakfast at Tiffany's

Audrey Hepburn was a classic actress with a number of beloved film credits. Breakfast at Tiffany's is definitely in that category, although she was 31 at the point of playing the 19-year-old character Holly Golightly.

Michael Rosenbaum, Smallville

Smallville was a popular series that served as a teenage origin story for Clark Kent/Superman. While the cast all portrayed teens during Season 1, some of them were a bit long in the tooth. Case in point: Lex Luthor actor Michael Rosenbaum who was actually 27 years old back in Season 1.

Ashleigh Murray, Riverdale

Riverdale's series finale aired in August of 2023, with the show running on The CW for seven seasons. Plenty of iconic Archie Comics characters appeared, including Josie McCoy. But despite playing high school sophomore, actress Ashleigh Murray was actually 28 when she fist appeared back in Season 1.

Cory Monteith, Glee

Glee became a huge hit when it premiered on Fox, and catapulted its cast of unknowns as full-blown TV stars. Late actor Cory Monteith starred as leading man Finn Hudson, but was 27 years old when debuting as his signature character.

Ross Butler, 13 Reasons Why

Netflix's 13 Reasons Why was a dark adaptation of the novel of the same name, and would eventually expand to a four-season run. Ross Butler played high schooler Zach, and was actually 26 years old back in Season 1.

Darren Barnet, Never Have I Ever

Never Have I Ever centers around 15-year-old girl Devi, and we watch various love stories play out throughout its run on Netflix. She has a huge crush on Darren Barnet's Paxton, who was 16. Although in reality the actor was 29 years old when Season 1 aired.

Judd Nelson, The Breakfast Club

The Breakfast Club is a quintessential '80s movie, and was released at the height of the Brat Pack's popularity. One of the leading characters was Judd Nelson's Bender aka The Criminal. But despite being in detention throughout the movie's runtime, Nelson was actually 24 years old when portraying that character.

Jennifer Grey, Dirty Dancing

Dirty Dancing features beloved performances by both Patrick Swayze and Jennifer Grey. The latter actress danced her heart out as Baby, although she was 26 years old rather than her character's 17.

Winona Ryder, Girl, Interrupted

1999's Girl, Interrupted was an Oscar winning drama that was a huge critical success. Winona Ryder starred as 18-year-old protagonist Susanna Kaysen, and provided a deeply moving performance. No one could have done it better, although she was truly 26 years old at the time of filming.

Nicola Coughlan, Derry Girls

Derry Girls is one of Netflix's many coming-of-age TV shows that is included on this list. The show follows a group of teenage girls, and all the hilarious mistakes that occur as they grow up. But actress Nicola Coughlan was actually 30 years old at the time of filming the show's first season.

Gabourey Sidibe, Precious

Lee Daniels' Precious is a truly harrowing film experience, one that elicits strong emotions for its title character, 16-year-old Claireece Precious Jones. Actress Gabourey Sidibe received wide acclaim for her performance in the movie, although she was actually 24 years old when she got the role.

Barbra Streisand, Yentl

Yentl is a masterpiece by Barbra Streisand, who directed, wrote, and starred in the acclaimed musical drama. But while her character was a young woman, she was actually 41 years old at the point of filming the acclaimed film.

Florence Pugh, Little Women

Greta Gerwig's Little Women movie was a huge hit when it arrived in theaters back in 2019. It got a bunch of major awards nominations, with Florence Pugh getting a Best Supporting nom at the Oscars for portraying Amy March. But while Amy was just 13 years old at her youngest point in the film, Pugh was actually 22.

Tobey Maguire, Spider-Man

Tobey Maguire was the first actor to play Spider-Man in live-action, before being followed by the likes of Andrew Garfield and Tobey Maguire. But while the latter actor was the most age appropriate, his predecessors weren't. Maguire was actually 26 years old while playing the teenager Peter Parker.

Despite the discrepancy between many of these actors and their characters, many of the actors listed above still crushed their roles. Although yes, some of these actors are somewhat infamous for being too old to portray teenagers. Still, smart money says this trend will continue with future TV and film projects.