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The 10 Most Rewatchable, Yet Absolutely Cringy '90s Rom-Coms

An electronic billboard has the title "Groundhog Day" with an image of the actor Bill Murray in an alarm clock face, a groundhog and actress Andie McDowell.
1993's "Groundhog Day" makes Erick Galindo's Top 10 list.
(Ethan Miller
Getty Images)
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I’ve always loved rom-coms, but they haven’t always loved me back. By which I mean, I hate the way they talk to me. And the way you cut your hair!

Erick Galindo's podcast takes you through those moments big and small that transform us forever.

OK. That’s a bastardization of a line from the poem by Julia Stiles’ character in 10 Things I Hate About You, a rom-com that teaches us that love can develop despite a weird scam where someone is getting paid to manipulate you.

See what I mean? A lot of the rom-coms I grew up with didn’t exactly show me a healthy way to be in a relationship.

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Listen to Episode 1

A Southeast L.A. Rom-Com: Erick Galindo tells Megan Tan a story about the wildest thing he did for love.
About this season
  • Season Two of LAist Studios' WILD podcast is out this week. We recommend you listen to Episode 1 as an accompaniment to this essay. The second season is all about the wildest things we do for love. It's a nine-part serialized rom-com for your ears. It centers a couple from Southeast L.A., who embark on a road trip adventure across America. Will their relationship survive the trip? Find out on WILD Season 2: I Think I'm Falling In Love, co-hosted by Erick Galindo and Megan Tan, and starring Melinna Bobadilla, Gabrielle Ruiz, and Atsuko Okatsuka.

I’m a '90s kid who grew up in Southeast Los Angeles. I was raised by two Mexican immigrant parents who were often too busy working their asses off to regulate what their kids were watching. And I watched a lot of things. Since I was kind of a misfit, film and TV were the places I turned to for escape but also for answers to questions like: What is romantic love?

And for some reason the '90s were a time when we thought love was kind of messed up (and very white) so like, just deal with it? Never mind that we didn’t get to see a lot of diversity and inclusion in the types of mainstream love stories that Hollywood was telling, but they were also frequently about unhealthy loops people were caught in. And because I was so eager to find my place in the world, and because life was also hard around me, this answer to what is romantic love made a lot of sense to me.

Whether it was a movie about a spoiled rich teen falling in love with her adult ex-step brother or a bunch of kids making a sex bet, or a jerk dying every night over and over again because he refuses to grow up, the romance I saw on the screen as I was coming of age really messed me up. But it was also very entertaining.

As an adult, with now two therapists, I’m not sure that was the best thing for my sex life but it definitely helped me develop a sense of humor and influenced me heavily as a writer. So I put together this list of 10 super rewatchable '90s films that heavily influenced our latest LAist podcast WILD: I Think I’m Falling in Love. The show takes the rom-com and marries it to the narrative podcast format.

These 10 films are cringy and sometimes problematic. And I hate that I love them so much but mostly I hate the way I don't hate them. Not even close. Not even a little bit. Not even at all.

10 Things I Hate About You

Year: 1999

  • Premise: An attractive teenager, played by Joseph Gordon-Levitt, pays an even more attractive but troubled teenager, played by the late, great Heath Ledger $500 to seduce the brilliant, beautiful, angry, nerdy Kat Stratford, played by Julia Stiles. It’s all so that JGL can date Kat’s younger, more popular, but also beautiful sister. And somehow it’s Shakespeare.
  • Favorite scene: The aforementioned poem scene where Julia’s character does her own interpretation of William Shakespeare’s “Sonnet 141” as a way to confess her love and forgiveness for Heath Ledger. Who, again, tricked her into dating him for five racks.
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She’s All That

Year: 1999

  • Premise: Latino teen icon Freddie Prinze Jr. plays the coolest guy in what looks like the school from Beverly Hills 90210. He gets dumped after his high school sweetheart cheats on him with a reality TV star. When a young Paul Walker makes fun of Freddie, they make a bet that Freddie can make even the geekiest girl in school prom queen. So they choose an art student with glasses played by Rachael Leigh Cook, who in real life is a model. Also Lil' Kim is in it!
  • Favorite scene: Arguably one of the most iconic scenes in rom-com history is Rachael Leigh Cook walking down the stairs while Kiss Me plays in the background, marking her full transformation from art geek to prom queen. Did I mention she’s a model!?


Year: 1995

  • Premise: Alicia Silverstone plays a rich, gorgeous popular kid (or a “virgin who can’t drive,” depending on who you ask) named Cher, who falls in love with her former step-brother Josh (played by Ant-Man himself Paul Rudd). And somehow it’s Jane Austen!
  • Favorite scene: Any scene with Donald Faison in it but especially when he takes Alicia Silverstone and Stacey Dash out for driving lessons and they accidentally get on the freeway.

The Wood

Year: 1999

  • Premise: The film is set primarily in Inglewood and takes place in two timelines: the '80s and '90s. It follows three friends played by Omar Epps, Richard T. Jones and Taye Diggs, who back in the '80s as teenagers had a bet on who would lose their virginity first. Now, as grown men in the '90s, they’re trying to get Taye Diggs’ character Roland over some commitment issues on his wedding day. It’s a coming of age story set in South L.A. There’s some guns, gangs, and cops, but it’s not the story, which is what growing up in the hood is like for the people there.
  • Favorite Scene: When Mike (played by Epps as an adult and by Sean Nelson as a teen) and Alicia (played by Sanaa Lathan as an adult and Malinda Williams as a teen) are about to have sex and Alicia’s gangster brother comes home and almost catches Mike stealing a condom from his room.

Out of Sight

Year: 1998

  • Premise: Jennifer Lopez plays a badass cop who accidentally witnesses a prison break by a criminal mastermind, played by George Clooney. They get into the trunk of a car together (she is his hostage) and vibe big time. Then they play cat and mouse for most of the film until they finally wind up together — sort of.
  • Favorite scene: The JLo and George Clooney meet-cute redux when the would-be couple/cop and criminal pretend to be strangers meeting for the first time at a hotel bar.

Fools Rush In

Year: 1997

  • Premise: A basic white dude played by Matthew Perry and an incredible Mexican American artist played by Salma Hayek have a one night stand that leads to an unplanned pregnancy that leads to a wedding that leads to a fake miscarriage that leads to a divorce that leads to Mexico that leads to Salma’s water breaking on the Hoover Dam!
  • Favorite scene: Matthew Perry proposing to Salma Hayek on their second sort-of date using the line, “somewhere between the tuna melt and your aunt’s tamales.”

Groundhog Day

Year: 1993

  • Premise: Bill Murray is a manchild of a TV weatherman who hates that he has to cover the Groundhog Day ceremony in Punxsutawney, Pennsylvania. Then he gets trapped in a time loop where he has to relive that same day over and over again, eventually finding increasingly clever ways to try to die by suicide. But no matter what he does, he still wakes up to the same day, until he falls in love with his producer, played by Andie MacDowell.
  • Favorite scene: All of them, basically.

Grosse Pointe Blank

Year: 1997

  • Premise: John Cusack plays a hitman facing an existential crisis on the verge of his high school reunion, where he realizes he’s still in love with his high school crush, played by Minnie Driver, whose dad is John’s latest execution target.
  • Favorite scene: John Cusack proposing marriage to Driver after a deadly shootout in her childhood home immediately after killing the final bad guy (Dan Aykroyd) by smashing him over the head with an old school TV set.

Reality Bites

Year: 1994

  • Premise: Four malcontent-college-buddies-turned-roommates played by Winona Ryder, Ethan Hawke, Janeane Garofalo and Steve Zahn struggle to find joy and pay the rent. OK. That’s an oversimplification. But also, they all seem deeply sad and hate Ben Stiller, who is happy and successful. Ethan Hawke’s Troy is the most sad and also a jerk who thinks he’s smarter than everyone. But somehow we’re all still rooting for him to steal Winona Ryder’s heart from Ben Stiller.
  • Favorite scene:  "Hello, you’ve reached the winter of our discontent."

Forget Paris

Year: 1995

  • Premise: The film starts in present day with Joe Mantegna telling a story (that flashes back and forth from past to present) about how Billy Crystal, an NBA referee, fell for an airline employee played by Debra Winger, after the airline lost his father’s casket and they went on their first sort of date at Billy’s father’s funeral.
  • Favorite scene: Referee Billy Crystal ejects real life Lakers legend Kareem Abdul-Jabbar (playing himself) from his “retirement tour” game.

Honorable mentions

The Wedding Singer, Blast From the Past, Never Been Kissed and every episode of Friends.

How do I find the WILD podcast?

It's now available from LAist Studios. Check it out wherever you get your get podcasts! Or listen to the first episode on the player above.

What questions do you have about Southern California?

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