Surprisingly Heartwarming Moments In Silly '90s Comedies

List Rules
Vote up the moments in wacky comedies that made you surprisingly emotional.

It may not seem like it (sometimes), but the '90s were a long time ago and a very different time; Bill Clinton was president, and Nirvana and Mariah Carey were everywhere. Regardless of your political sensibilities or taste in music, one thing is undeniable: The '90s were a watershed decade for comedic films. On top of Saturday Night Live's inimitable group of stars, Robin Williams and Jim Carrey were some of the biggest box-office draws, while writer/director John Hughes continued making audiences feel things. All of these are perfect examples of creatives who brought depth to characters and films that would otherwise be written off as silly - a word that often describes the absurd or foolish.

And, as we know, the best sort of comedy deals in truth. This list compiles surprisingly heartwarming or emotional moments that punch you in the gut in movies that are otherwise pretty wacky. While there’s a fine line between heartwarming and heartbreaking, these '90s films manage to walk that tightrope... if only for a moment. 

  • Tommy Boy sees Tommy Callahan embark on a quest to sell enough brake pads to save his late father’s auto business, with the help of his father’s tightly wound assistant, Richard Hayden. As a silly road-trip flick, the magic of Tommy Boy is reliant on the incredible chemistry and dichotomy between Chris Farley and David Spade’s characters. While Tommy is dimwitted and lovable, Richard is apathetic, belittling the former throughout most of the film. Suffice to say, Richard doesn’t have many friends - which he admits at the end of the film. 

    Before Tommy sells half a million brake pads and saves his father’s company, there’s a moment where he believes he’s failed to stop that buyout. Near the end of the film, Richard attempts to cheer Tommy by telling him, “Hey, you did your best. When we started this thing, I thought you'd just walk through this like you walk through everything else, but you didn't. Your dad would've been proud of you. And you got a friend out of it. Now I know it's no big deal to you since you have so many, but... I don't.” 

    873 votes

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  • The children in Kevin McCallister’s neighborhood (or maybe just Buzz) refer to Old Man Marley as a serial killer, the South Bend Shovel Slayer. Sometime after Kevin’s family leaves him home alone, and said home becomes threatened by the Wet Bandits, Kevin runs into Marley at the local church, where his granddaughter is rehearsing with her choir for Christmas mass. The shovel-wielding rumors are put to rest in the resulting conversation, in which Marley explains an estranged relationship with his son following a heated argument. Kevin suggests Marley should call his son and reunite with his family.

    While this moment gets overshadowed by Kevin’s battle with Harry and Marv, Marley does save Kevin near the end of the film. In easily the most heartwarming moment in the history of the Home Alone franchise, Kevin reunites with his family just as Marley meets up with his family - hugging his daughter-in-law and granddaughter as Kevin looks on with a wave and a smile. 

    703 votes

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    605 VOTES

    In ‘There’s Something About Mary,’ Ted Says A Very Casual Goodbye To Warren, Who’d Never Warmed Up To Anyone Before

    Ted’s dream date with the titular Mary never happens due to the worst kind of injury a man can imagine (if you know, you know). Later in life, Ted decides the only way he can fulfill his wildest dreams is to stalk the girl next door, Mary. So, he hires a private detective to track her down. Naturally, Mary has a slew of other stalkers. On the surface, none of this sounds heartwarming.

    Enter Warren, Mary’s neurodivergent brother who develops a rather touching relationship with Ted. In fact, the main reason Mary is interested in Ted is that he once protected Warren from bullies when they were kids. Near the end of There’s Something About Mary, Ted removes one of Warren’s headphones so he can say goodbye. While it may not seem like much, Warren has always reacted badly anytime his ears were touched. He trusts Ted. Irrespective of the many jokes at Warren's expense in the film, the aforementioned subtle moment is undeniably touching.

    605 votes
  • Mrs. Doubtfire follows Daniel Hillard, who becomes desperate to spend time with his family after his ex-wife, Miranda, is granted sole custody of their children. Naturally, the struggling actor decides to disguise himself as a geriatric English woman and get hired as Miranda’s nanny, Mrs. Doubtfire. Watching the movie for the first time, one might assume the Mrs. Doubtfire shtick would eventually win Daniel back his family. Unlike other family comedies, Mrs. Doubtfire chooses a route more in line with real-life divorce. 

    Near the end of the film, Daniel, as television’s Mrs. Doubtfire, ala Mr. Rogers' Neighborhood, answers a letter from a young girl whose parents just split up. Mrs. Doubtfire tells her, “Just because [your parents] don't love each other anymore, doesn't mean that they don't love you.” This monologue continues as Daniel picks up his kids for one of their regular, unsupervised visits, and drives off into the proverbial sunset. If you were a child of divorce in the '90s, Mrs. Doubtfire’s message about unconventional family dynamics was one you needed to hear. 

    704 votes

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  • When Scott Smalls moves to the Los Angeles suburbs in 1962, he befriends the boys who play baseball at the local sandlot and is taken under the wing of prodigy Benny Rodriguez. The boys all fear “the Beast” - an English mastiff who resides on the other side of the sandlot’s fence. Or rather, a monster who eats children. The kids lose many balls over that fence and, of course, Smalls's stepfather’s Babe Ruth-signed ball is lost, as well. 

    This is when Benny goes over the fence to retrieve it, which results in Beast chasing him through town. When they finally return to the eponymous lot, Benny jumps the fence before the Beast crashes into it, causing it to fall and land atop the so-called “monster.” Smalls and Benny then lift the fence to free their supposed enemy - which leads to their encounter with the Beast’s owner, Mr. Mertle. (It turns out the Beast's real name is actually Hercules.) Mr. Mertle gives Smalls a ball autographed by all of the 1927 New York Yankees and the movie ends with a silly, but appropriate, happily ever after. 

    517 votes
  • Inspired by William Shakespeare’s The Taming of the Shrew, 10 Things I Hate About You sees Patrick accept a bribe to date Kat Stratford, a sarcastic, smart teen whose love life directly influences whether or not her younger sister can date. The film is named after the poem Kat writes after finding out about Pat’s duplicity.

    While it could be seen as sad, or overly sappy, when Kat lists all of the things she hates about Pat and then reveals she doesn’t hate him at all, it comes off as sincere, touching, and heartwarming, and it propels the film’s happy ending. We all make mistakes, especially in high school. 

    490 votes

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