Top 10 Times Nice Guys Did NOT Finish Last

“The Mask” (1994)

Jim Carrey made himself a star by playing Stanley Ipkiss, a socially awkward but sweet man who works at a bank. Stanley is often ridiculed for his insecurity, and he doesn’t have many friends as a result. He quickly falls for the gorgeous Tina Carlyle, who visits the bank to scope it out for her gangster boyfriend, Dorian Tyrell. Stanley eventually wins over Tina, securing her love with the type of kindness and affection that she never received from Dorian. In the end, Stanley and Tina become romantically involved, with the otherwise meek Stanley attaining a good degree of self-confidence through his time with The Mask.

“Juno” (2007)

This movie came out shortly after “Superbad” and helped establish Michael Cera’s schtick as the timid and softly-voiced funnyman. Like many of Cera’s characters, Paulie Bleeker is shy, quiet, and mild-mannered. He often absorbs Juno’s frustrations with resigned acceptance, and he remains loyal to her even in the face of her indifference. Juno isn’t sure that she loves Paulie, but Paulie loves Juno with all his heart. He is there for her, even when she’s playing the tough girl and pretending not to need his comfort. Luckily, Juno eventually learns to open her heart to Paulie and she admits that she loves him. Paulie obviously reciprocates, and the two enter into a stable relationship.

“Back to the Future” (1985)

This is as much George’s movie as it is Marty’s. After traveling back to 1955, Marty makes the not-so-surprising realization that his father is an outsider. He doesn’t have any friends, he gets mistreated, and he acts much like a stereotypical ‘50s nerd. He pines for the cute and sociable Lorraine Baines, who at first seems way out of his league. But with the help of his own cool son, George becomes more confident and actually begins standing up for himself. He punches Biff and acts in a protective manner at the dance, which eventually wins the heart of his crush. The two marry and live happier lives as a more confident and loving couple.

“She's Out of My League” (2010)

The title of this movie says it all. Kirk Kettner is played by Jay Baruchel, who has been typecast as the adorable but awkward man. He is very nice and very cute, but his mumbly voice and obvious insecurities don’t exactly scream confidence. He’s attracted to the beautiful and personable Molly McCleish. Within the movie itself, Kirk is labeled a 5 and Molly a 10, and no one genuinely believes that they will get together. And they actually do break up at one point; Kirk thinks there needs to be something “wrong” with Molly, and Molly admits that she finds Kirk “safe.” But in the end, Molly accepts Kirk for who he is, and the nice guy gets the hot girl.

“Spider-Man 2” (2004)

This superhero film was quite revolutionary for its time, as it took its story and characters seriously. Brilliant character writing was mixed in with the fun superhero action, and it actually looked at the consequences of being a famous crime fighter. Peter is estranged from Mary Jane for much of the movie, mostly due to the stress and necessities of being Spider-Man. He’s never present, and when he is his mind is elsewhere. The ending again subverts expectations, and Peter’s identity as Spider-Man is revealed to Mary Jane. She finally understands his behavior, and this understanding allows her to break free from John Jameson and run, quite literally, into Peter’s arms. She knows that Peter will always be Spider-Man, but she accepts it.

“Forgetting Sarah Marshall” (2008)

As the title suggests, this movie is about getting over a break-up. That, and finding a new love. Peter Bretter is a likable but childish television composer who is dumped by his girlfriend, Sarah Marshall. He takes a trip to Hawaii in an attempt to get over the break-up and meets a nice and attractive hotel receptionist named Rachel Jansen. There’s just one problem - Sarah and her new boyfriend are staying at the same resort. Luckily, time, fun Hawaiian experiences, and Rachel all combine to help Peter find mental clarity. He gets over Sarah, cleans himself up, becomes more ambitious, and yes, he even gets Rachel.

“Harry Potter” franchise (2001-11)

We like to pretend we’d be Harry or Hermione, but we’d probably be Neville. He’s not especially smart, not especially talented, and not especially popular. Even though he's grown up in the Wizarding World, he’s even less inclined towards magic than Harry. But he’s nice, he’s friendly, and he discovers a certain sort of heroism throughout the films. He’s the one who stands up to Voldemort in the courtyard, and he’s the one who kills Nagini with the Sword of Gryffindor. And while it’s not made explicitly clear in the films, Neville also gets the girl. He eventually becomes Herbology professor at Hogwarts and marries a fellow Dumbledore’s Army member named Hannah Abbott. How adorable is that?

“Free Guy” (2021)

Ryan Reynolds does it again with “Free Guy,” a fun comedy with a brilliant premise. He plays Blue Shirt Guy, a random NPC inside a video game. Guy develops a romantic interest in Millie Rusk, who plays the game as Molotov Girl. She is looking for source codes, which were stolen and hidden by the game’s creator, Antwan Hovachelik. The source codes are for a game that she and a friend named Keys had developed together. They eventually find the codes and launch a game called “Free Life.” But in the end, Guy reveals that his romantic interest in Millie was actually pre-programmed by Keys. Realizing that he made Blue Shirt Guy as a love letter to her, Millie embraces and kisses Keys.

“The Lord of the Rings” franchise (2001-03)

Samwise begins life as any other hobbit. All he wants is to live in peace in Hobbiton, tend to his gardens, and go to the pub to drink and shyly admire the bartender, Rosie Cotton. The only problem is that Sam is way too shy to make a move. Well, that all changes after the War of the Ring. Sam safely returns home and realizes that approaching Rosie is nothing compared to facing down Gollum, Ringwraiths, giant spiders, and the forces of Mordor. After taking a drink to ease his nerves, he approaches Rosie and finally makes his move. We don’t see the interaction itself, but the two eventually marry and have children, so whatever Sam said clearly worked!

“The 40-Year-Old Virgin” (2005)

While Andy Stitzer is 40 years old, “The 40-Year-Old Virgin” serves as the perfect coming-of-age comedy. Andy is portrayed as a man-child. He spends his nights alone in his apartment reading comics, painting figurines, playing video games, and doing karaoke by himself. His co-workers discover that he is still a virgin, so they embark on a mission to get him some. But the movie has a wonderful heart, and it places love and companionship over quick physical satisfaction. Andy falls for single mother Trish, and she teaches him how to embrace adulthood. Andy eventually has sex, but the moment isn’t really played as a victory; the victory is in his finding of love and maturity. The nice guy wins in every way.