Malcolm in the Middle — “Dewey’s Dog” (Season 3, Episode 17)
Hal and Lois are one of the greatest, most realistic, and completely insane couples on television. Constantly overwhelmed with their sons and busy work days, they rarely have time to themselves. Hal plans a romantic night for Lois and shows up in the break room at her retail job with a boombox playing Rod Stewart’s “Tonight’s the Night (Gonna Be Alright).” Unfortunately, she can’t leave work and Hal ends up riding in a limo with a sick Craig.
South Park — “Raisins” (Season 7, Episode 14)
Inspired by Trey Parker’s real life breakup, Wendy breaks up with Stan in this episode, sending him spiraling into a depression. He’s determined to get her back but doesn’t know how. A friend advises him to do the most romantic thing he can think of: “Stand outside her window, hold a boombox over your head, and play Peter Gabriel.” But because this is South Park, Stan plays “Shock The Monkey” and Wendy disappears with a different boy.
The Simpsons — “It’s a Mad, Mad, Mad, Mad Marge” (Season 11, Episode 21)
The Simpsons has parodied just about every classic movie out there, and Say Anything… is no exception. It’s been mentioned a few times: a parody of the final airplane scene, an Itchy and Scratchy cartoon titled “Spay Anything,” and an episode called “Pray Anything.” This particular scene shows up in Season 11 when Otto proposes to his girlfriend (voiced by Parker Posey) by holding up a boombox and playing “Every Rose Has Its Thorn” — getting so into the song that she almost doesn’t get to say yes.
Gravity Falls — “Gideon Rises” (Season 1, Episode 20)
In the Season 1 finale of Gravity Falls (a show everyone should be watching), the town of Gravity Falls finds itself thrown off course because of Gideon. In one light moment, breaking the tension when Wendy sadly reveals she might have to leave, goth teen Robbie randomly pops up with a boombox, causing Wendy to flee in the opposite direction — and Robbie to chase after, boombox still in hand.
Everybody Hates Chris — “Everybody Hates Homecoming” (Season 4, Episode 3)
Neighborhood kid James has a crush on Chris’ sister Tonya, and spends much of the series flirting with her, to no avail. Eventually, he goes the desperate Say Anything… boombox route, but chooses George Michael’s “Careless Whisper” over Peter Gabriel. But it’s Tonya’s father (Terry Crews) who comes downstairs to explain to James that, “You can’t make somebody like you back.”
Glee — “Girls (and Boys) On Film” (Season 4, Episode 15)
How did it take 81 episodes for Glee to do a “In Your Eyes” scene? This episode features performances of songs from multiple classic movies (“Danger Zone,” “Old Time Rock & Roll,” and “Shout!” are a few) but the centerpiece is when Will shows up at Emma’s house, with a boombox and wearing a Lloyd Dobler-like coat, and performs “In Your Eyes” with New Directions.
Saturday Night Live — “Joseph Gordon-Levitt/Dave Matthews Band” (Season 35, Episode 7)
Joseph Gordon-Levitt perfectly embodies Lloyd Dobler’s mannerisms in this sketch. It’s a recreation of the famous boom box scene except with an obnoxious neighbor (Jason Sudeikis) popping up to distract him, needling him, and generally questioning what the hell Dobler is doing.
Dog With A Blog — “Guess Who Gets Expelled?” (Season 3, Episode 1)
Not even Dog With A Blog is exempt from the Say Anything treatment. These kids have no idea what they’re parodying, and neither do the children who watch the show, but the humor of Chloe’s boyfriend playing an awful children’s song — one that she doesn’t even like — still translates. But maybe next time, the dog can do it.