Sometimes, actors are chosen for roles that seem far too mature for them. Bad language, extreme violence, or uncomfortable scenes make us wonder if the stars are really mature enough or ready enough for the roles they’re playing.
On the other side of the coin, we have actors who are far too old for the roles they’ve been cast in. Adults playing high school students is a well known example, giving many of us unrealistic and unfair expectations of who we’d become and who we’d meet when we hit our teenage years. (Where are all the acne, braces, and awkward growth spurts?) Sometimes, these casting decisions are forgivable, or even unnoticeable. Other times, the age discrepancies between the actors and the characters they play are too vast not to make an impression.
20 Colin Farrell in Alexander (28 vs. 16)
The movie Alexander was a hot mess for a lot of reasons, but one of the biggest may have been the major age difference between the real-life conqueror (who was 16 at the time of his first military victory) and the actor who played him (Farrell was 28 at the time). The even bigger issue, though? Casting the 29-year-old Angelina Jolie to be Farrell’s mother!
19 Shirley Henderson in Harry Potter and the Chamber of Secrets (36 vs. 14)
There was a reason audiences everywhere collectively cringed when we saw the ghostly Moaning Myrtle sidle up to Harry Potter while he took a bath in Harry Potter and the Goblet of Fire: the actress was pushing 40 at the time! Despite all the makeup and CGI, actress Shirley Henderson was way too old to play the deceased young teen.
18 Sean Patrick Thomas in Save the Last Dance (30 vs. 17)
Giving unfair expectations to high school girls everywhere, Sean Patrick Thomas was one of many adult celebs who played high school students on screen. In Save the Last Dance, Thomas was 30 years old, while his love interest – played by Julia Stiles – was about 18 at the time of production, making the age difference between the pair much more noticeable.
17 Stacey Dash in Clueless (28 vs. 16)
Unlike some of her other Clueless co-stars (with the exception of the ageless Paul Rudd), Stacey Dash simply doesn’t age! This might explain why the then-28-year-old was able to pass for a high school sophomore. Dash managed to play a high schooler so convincingly that she stuck around for the spinoff series, despite being into her 30s!
16 Jimmy Stewart in It’s A Wonderful Life (38 vs. 19)
In all fairness to the casting department behind the holiday classic It’s A Wonderful Life, the characters stick around for decades. However, that doesn’t excuse the fact that they chose Jimmy Stewart – a man with more than a few wrinkles and a receding hairline at age 28 – to play a teenager hoping to travel the world and go to college!
15 Jennifer Grey in Dirty Dancing (27 vs. 17)
It’s a testament to Jennifer Grey’s acting skills that we all believed her performance as the fresh-faced 17-year-old Baby in the classic Dirty Dancing. The role is easily the most iconic for Grey, and since it saw her burst onto the Hollywood scene, it may have been why we were able to forget that she was actually 27 at the time.
14 Calista Flockhart in The Birdcage (31 vs. 18)
More of an indication of the buttoned-up nature of her character, Calista Flockhart certainly dressed beyond her years in The Birdcage, when she played an 18-year-old student, but in reality, the actress was 31! Of course, we were able to forget the age discrepancy since she resided in the background to Nathan Lane’s and Robin Williams’ theatrics.
13 Rachel True in The Craft (29 vs. 16)
Much of the supposedly high school-age cast in The Craft was in their early twenties during filming, which is normal for a movie like this. One outlier, however, was Rachel True, who was 29 at the time, and a good few years older than the rest of her castmates! We’ve got to give it up to True for holding her own and pulling off a convincing Catholic schoolgirl!
12 Alison Lohman in White Oleander (23 vs. 15)
Another newcomer (at the time) to the Hollywood scene was Alison Lohman, whose youthful features saw her cast in multiple films as a girl much younger. While she played the 15-year-old Astrid in White Oleander, Lohman was 23. In Matchstick Men, she was 24 to her character’s 14; in Flicka she was 27 to her character’s 16!
11 Gabrielle Union in Bring It On (27 vs. 17)
Gabrielle Union has been blessed with an ageless visage, and it’s something that has worked to her advantage, as she’s been cast in multiple movies that have her playing characters many years younger. One of the most famous would be when she starred in Bring It On, at the age of 27 playing a 17-year-old cheerleader!
10 Kevin Spacey in Beyond the Sea (45 vs. early 20s)
Easily a vanity project, actor Kevin Spacey chose not to be concerned about the reality of age when he cast himself as Bobby Darin in Beyond the Sea. Spacey was 45 at the time of filming and yet opted to play the late singer during his 20s and 30s. Even all the heavy makeup can’t detract from the fact that Spacey is working with more than a few wrinkles.
9 Barbra Streisand in Yentl (40 vs. 17)
As lauded as it may be and as talented as she is, there’s no amount of makeup or heavy filters in the world that can truly make audiences believe that Barbra Streisand – who was 40 at the time – could pass as a 17-year-old girl disguising herself as a 15-year-old boy. It won many awards, but even the strongest performer isn’t that convincing.
8 Matt Damon in Behind the Candelabra (42 vs. 17)
Matt Damon may have boyish good lucks and an effortless charm, but there’s absolutely no way that anyone could compare him and a regular high school student and believe them to be the same age. In 2013’s Behind the Candelabra, Damon played Scott Thorson, the younger lover of Liberace, and while Damon was great, the age discrepancy was too huge not to notice.
7 Andrew Garfield in The Amazing Spider-Man (28 vs. 17)
With his lanky figure and puppy-dog eyes, one could squint and maybe believe actor Andrew Garfield to be a high school student in The Amazing Spider-Man. However, when you’re actually watching the movie, no amount of special effects can disguise the fact that Garfield was 28 at the time he was supposed to play the young Peter Parker.
6 Tobey Maguire in Spider-Man 3 (32 vs. late teens)
Like Garfield, Tobey Maguire was in his late twenties when he was cast in the first Spider-Man. By the time the third instalment of the franchise rolled around, though, the actor was in his early 30s and those big blue eyes couldn’t distract from the fact that he was way too old to be playing the teenage Peter Parker.
5 Alan Ruck in Ferris Bueller’s Day Off (29 vs. 17)
As Cameron in Ferris Bueller’s Day Off, Alan Ruck doesn’t seem like your typical teenager, and acts more like a stick-in-the-mud. There’s a good reason for that: during filming, Ruck was more than a decade older than his actual character, at 29! Even Ruck admitted that he was surprised he got the part, but said, “When I was 18, I sort of looked 12.”
4 Olivia Newton-John in Grease (29 vs. 17-18)
Perhaps the reason Olivia Newton-John looked so much better in her black leather makeover was because the more mature look suited the actress – she was 29 at the time! The ponytailed, poodle-skirted early look of Sandy was just too young for the almost-30-year-old actress to pull off. However, there was one costar who was even older than Newton-John during filming.
3 Stockard Channing in Grease (33 vs. 18)
Olivia Newton-John’s co-star in Grease, Stockard Channing, may have been facing some high school dilemmas, but Channing was way past the era of lockers and school dances – she was 33! As the leader of the Pink Ladies, Channing had some street smarts that belied her age, but there’s no way we would’ve taken her for a high school senior.
2 Roger Moore in A View To A Kill (58 vs. 30s/40s)
No, that’s not a grandfather with his beautiful granddaughter – audiences were actually supposed to believe that the 58-year-old Roger Moore would be able to get with a woman half his age without anyone raising an eyebrow! Considered to be too old to play James Bond, Moore upped the ick factor by bedding women young enough to be his daughter or granddaughter.
1 Rachel McAdams in Mean Girls (25 vs. 17)
Comparing them now, it’s difficult to believe that Rachel McAdams is actually seven years older than her Mean Girls co-star Lindsay Lohan (McAdams is 40 while Lohan is 33). That age-defying quality did her well when she was cast as queen of the Plastics when she was 25 opposite her teenage co-stars. In fact, her on-screen mom Amy Poehler was only seven years older than her!