Surprisingly Heartwarming Moments In Silly '90s Comedies

Josh Plainse
March 4, 2022 41.8K views
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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.” 

    817 votes
  • 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. 

    667 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. 

    665 votes
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    567 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.

    567 votes
  • 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. 

    485 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. 

    462 votes
  • Groundhog Day essentially created its own genre in which a character lives the same day over and over until they either accomplish a goal or learn some sort of lesson. The original film sees its cynical TV weatherman (played by the inimitable Bill Murray) indefinitely trapped in the small town of Punxsutawney for the same 24 hours - which he uses to try and get laid (among other things). Partway through the film, Phil realizes that his love interest, Rita, is too good for him. While she sleeps, he tells her: 

    I don't deserve someone like you. But if I ever could, I swear I would love you for the rest of my life. 

    Afterward, he stops telling Rita about the time loop and doesn’t focus on wooing her. The moment acts as the linchpin for all the uplifting moments that follow, propelling Phil to be the best version of himself - one worthy of Rita. 

    319 votes
  • After being abandoned at the altar, Robbie Hart must go back to work as a wedding singer - a job that reminds him of the worst day of his life. While this film is filled with many emotional moments, including its central romance, perhaps the most heartwarming moment comes courtesy of the late Ellen Albertini Dow’s Rosie, best known as The Wedding Singer’s rapping grandmother.

    That being said, Rosie’s musical talents aren’t limited to “Rapper’s Delight.” Throughout the film, Robbie gives Rosie singing lessons and, at her 50th anniversary party, those lessons pay off as she serenades her husband with “Till There Was You.” 

    425 votes
  • The only reason Billy Madison made it through school was his father’s affluence. In short, he’s very spoiled and spends most of his time nursing hangovers, and his father has had enough. Therefore, hotel magnate Brian Madison forces Billy to retake and pass every grade in 24 weeks. While doing so, Billy grows as a human being courtesy of the silly.

    Early on in his educational journey, in perhaps the moment that first makes the character likable, Billy pretends to pee his pants to save a kid named Ernie from being embarrassed by the other children. The adult Billy explains to the rest of the third grade, “You ain’t cool unless you pee your pants.” 

    442 votes
  • Everyone wants to be “cool” growing up. Especially Chazz Darby, who became a metalhead rocker, and then holds a radio station hostage just so he and his friends can have their band’s demo tape played on the air. When a bunch of people tailgate the hostage situation, including Chazz’s cliche LA girlfriend, Kayla, Chazz admits the unthinkable: He hasn’t always been cool. In fact, he “was a geek in school,” had really short hair, and played Dungeons & Dragons. He even ate his boogers and had a bug collection.

    On top of that, his real name is Chester - the metal persona stems from his desperation for love and acceptance. Naturally, this prompts the crowd to list all of the things that made them uncool: Lemmy admits to being the editor of the school magazine while another man wore corduroy pants. While the implication that D&D is uncool is uncalled for, the crowd supporting Chester’s misplaced insecurities is... heartwarming? 

    216 votes
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    264 VOTES

    In ‘Wayne’s World,’ Wayne And Garth Hang Out By the Airport And Open Up A Bit

    Rock enthusiasts Wayne Campbell and Garth Algar host the public-access television show, Wayne’s World, in Wayne's parents' basement in Aurora, IL. Outside of being hilarious, Wayne’s World (the movie, not the fictional public-access show) is really about the innocence of small-town friends Wayne and Garth - something exemplified by a scene in which the pair hang out by the airport, talk about life, scream at planes as they fly overhead, and laugh hysterically.

    While short and subtle, the scene is heartwarming, especially considering Mike Myers’s genuine laughter at Dana Carvey’s improvised line, “Did you ever find Bugs Bunny attractive when he put on a dress and played a girl bunny?” 

    264 votes
  • Lloyd Christmas and Harry Dunne very much, albeit unintentionally, abide by the proverb "ignorance is bliss." One of the things these friends don’t seem to be aware of is that although they don’t have much, they have each other. At the beginning of the film, Lloyd (very briefly) opens up to his best friend about how lonely he actually feels. He tells Harry, “You know what I'm sick and tired of, Harry? I'm sick and tired of having to eke my way through life. I'm sick and tired of bein' a nobody. But most of all... I'm sick and tired of havin' nobody.” 

    That monologue is what convinces Harry to accompany Lloyd to Aspen, “a place where the beer flows like wine,” where they can find Mary, return the briefcase full of money, “plug [themselves] into the social pipeline,” and live happily ever after. In a weird, silly way, Lloyd's admittance foreshadows Dumb and Dumber’s central lesson - if one were to call it that. 

    195 votes