Top 10 Most Rewatched 90s Rom-Com Moments
#10: "I Wanted It To Be You" “You've Got Mail” (1998)
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Tom Hanks and Meg Ryan could be considered the “it couple” of 90s romcoms, having starred in three romantic comedies from 1990 to 2000. Their first one, “Joe Versus the Volcano'' wasn't very well received, but their subsequent romantic collabs are two of the most successful and beloved of the decade. While we’ve definitely rewatched the Empire State Building scene from “Sleepless in Seattle” a few times, it’s the “You’ve Got Mail” happy ending that had to make this list. The audience has known that they were each other's online pen pals the whole movie, but when Hanks and Ryan finally learn the truth it’s a moment of pure romcom magic. Even the dog approves.
#9: First Kiss on the Pitcher's Mound “Never Been Kissed” (1999)
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Josie Geller waited a long time for a kiss worth remembering. When the moment arrived it was all that she dreamed and more. Josie’s first real kiss is one the entire city of Chicago will never forget. It was definitely a bold move to put her heart out on the line like that, or the pitcher’s mound rather. No matter how many times we’ve seen this movie, we can’t help but get a little nervous watching that clock countdown. Or feel crushed when it hits zero. But our hearts go soaring again right along with the crowd when Sam finally shows up. No apology, necessary, Sam.
#8: Sign Language “Four Weddings And A Funeral” (1994)
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It’s usually the big romantic confession that’s the most rewatched. In the case of “Four Weddings And A Funeral” that honour goes instead to the scene that leads to that “I love you” moment. In real life, the “speak now or forever hold your peace,” line at a wedding is just a formality, but in movie land is when memorable moments often occur. This one comes courtesy of David, who is deaf. By having him sign his objections it forces Charles to translate and speak his truth out loud. The vicar asks if this suspicion is true, and like the guests at the wedding, we the audience hold our breath in anticipation. We’re over the moon, though we understand why Henrietta might not be.
#7: Glasses Off “She’s All That” (1999)
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How does it feel to be a trope? There aren’t many people who can answer that question, but Rachel Leigh Cook is one of them. Like so many before her, Laney Boggs becomes the subject of a classic romcom makeover. Glasses off and we’ve got us a whole new person. In fact, this scene has now become one of the most recognizable examples of this trope in action. It was even parodied just a couple years later in “Not Another Teen Movie.” Although it's hard to miss the sexist undertones of the scene these days, it’s iconic place in romcom history can’t be denied.
#6: "A Better Man" “As Good as It Gets” (1997)
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Romantic comedies generally don’t get the same kind of Academy Awards love that dramatic films do, but one exception in the 1990s was “As Good as it Gets.” Both Jack Nicholson and Helen Hunt won acting Oscars for their performances in the film. While they took home statues we took home one of the great romcom lines of all time. It starts off a little questionably. Nicholson’s Melvin seems to be rambling about things that have little to do with Hunt’s character Carol. But a little patience pays off in a big way. Melvin’s clarification stops Carol in her tracks. This line made anything men said to their women for the next decade pale in comparison.
#5: Subway Ring “While You Were Sleeping” (1995)
Imagine saving a handsome stranger's life and when he wakes from his you get married. Sounds crazy, right? Well, even cazier is the fact that Sandra Bullock’s Lucy fell in love with his brother, Jack instead. The awkward triangle situation culminates in an almost-wedding, with Lucy coming clean about everything that led to that moment. Just when it seems like everything is ruined though, Jack shows up to deliver the kind of romcom moment that makes our hearts flutter. With his family cheering him on, he steps inside the subway booth to formally propose. It’s a sweet finale for this modern CTA love story.
#4: “I Say a Little Prayer” “My Best Friend's Wedding” (1997)
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When it comes to this movie, it’s a moment of comedy, rather than romance that we find ourselves rewatching over and over again. It also doesn’t hurt that the scene involves a super catchy song as well. George and Jules’ dining companions are only too eager to join in on this musical moment, enthusiastically singing along to a bemused Jules. It gets even better when the mood spreads through the restaurant. Watching the entire room stage an impromptu musical number, there’s no way you’ll be able to keep the smile off your face. Or keep the song out of your head for the rest of the day. You’re Welcome.
#3: "Just a Girl" “Notting Hill” (1999)
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Hugh Grant’s Will is not initially keen to give things another go when Anna, played by Julia Roberts, walks into his bookstore again. We get it. Relationships are hard enough on their own, but Anna’s celebrity status added a whole new layer of issues. Will doesn’t see how their lives could ever be compatible. Anna respects his decision, but can’t go without making her final case. She opens herself up completely to make a declaration that has now become famous. It’s heartbreaking to see Will let her walk out after that, but we comfort ourselves knowing it will all work out in the end. Meanwhile, this scene itself has become one of the most iconic in the genre.
#2: Heath Ledger Singing “10 Things I Hate About You” (1999)
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Is there any gesture more romantic than a serenade? Well, how about a serenade in front of the entire high school girl’s soccer team accompanied by the school’s marching band? There’s no doubt that this moment played a huge part in Heath Ledger’s breakout following the film’s release. Who wouldn’t fall in love with him after a stunt like this? The moves, the smile...Julia Stiles’ Kat didn’t stand a chance. As a modern retelling of Shakespeare’s “The Taming of the Shrew,” “10 Things” stays true to the spirit of the play while adding scenes like this that have made the film a classic in its own right. We feel like the Bard would love this musical moment as much as we do.
#1: “You Had Me At Hello” “Jerry Maguire” (1996)
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Few films from the 90s have given us more iconic lines of dialogue than “Jerry Maguire.” The film is a treasure trove of quotables that have stood the test of time and are still recognizable more than two decades later. But there is one line that stands out above them all, and we all know what it is. No, no. The other one. When Jerry shows up to see Dorothy, it’s intended to be the romcom Big Speech moment that always wins back the love interest. He’s clearly prepared to really go for it, but Dorothy makes it clear that it’s not necessary. It’s a coy little play on a genre trope by writer/director Cameron Crowe, and it might be even better on the rewatch.
