The Ex Files: TV's 15 greatest recurring exes

Has there ever been a creepy bit of dialogue more perfectly suited for Jon Lovitz’s patented delivery than the following? “Marge, I would appreciate it if you didn’t tell anybody about my busy hands. Not so much for myself, but I am so respected, it would damage the town to hear it. Goodnight!” We’re hard pressed to think of another (Lovitz also played a stalker version of himself to similar gross comedic effect on ), and the actor’s vocal calling cards make him a wonderful foil to Homer, driving home the point that he’s his opposite in just about every way (sincerity, money, physical stature, ego). And for all of Homer’s many, many faults, Marge made the right choice. [Tim Lowery]

The – is largely built on a swirling vortex of recurring exes. It was Sam and Diane’s on-again, off-again relationship that brought (Kelsey Grammer) into the fray, and when he became Diane’s ex, Frasier married Lilith Sternin (Bebe Neuwirth). By the time he had his own spinoff, Lilith was a recurring specter, showing up once or twice a season to remind her ex-husband what he left behind and maybe to propose getting back together. Lilith was cool in the classical sense of the word—that is, cold. Her detached, icy demeanor made her an outcast for the rest of the Crane clan, but a favorite for audiences for nearly two decades—and again on Paramount+’s . [Drew Gillis]

“Oh! My! God!” With those three words, delivered pitch-perfectly by , all nasal tone and hand movements, became ’ most memorable ex. With apologies to everyone else who recurred on the show as a former partner of the six leads, anytime Janice pops up you just know a lot of laughter is about to ensue. As ’s () on-again, off-again girlfriend, she appears randomly throughout the NBC sitcom’s 10-season run. Everything about Janice is heightened: her voice, her outfits, and her overbearing nature. She’s always fun to have around. [Saloni Gajjar]

Whether or not you agree that ’ Jess Mariano () was Rory Gilmore’s (Alexis Bledel) best boyfriend (he was!), there is no doubt he was her best ex. Sure, things got off to a rocky start, as he calls her like a creepy stalker from California, declares his love out of the blue, and tries to get her to run away with him. But their time apart allowed Jess to grow and mature—and to swoop in when Rory needed someone who knew her deeply to shake some sense into her. See the “Why did you drop out of Yale?!” speech or his encouragement of her book in A Day In The Life for proof. As a boyfriend, Jess could be flaky, emotionally unavailable, and immature. As an ex, he became a confidant, a sounding board, and a much-needed voice of reason in Rory’s life. [Mary Kate Carr]

If had better planned its seasons-long love triangle between and Brooke (), then maybe Peyton could’ve ended up with someone really freaking good: Jake Jagielski (Bryan Greenberg). Instead, Jake became a recurring ex, appearing in multiple episodes between seasons one and three. His chemistry with Peyton aside, Jake was certain of his love for her, unlike a constantly wavering Luke. That alone makes him a better candidate. [Saloni Gajjar]

Her? Yes, her! (played by Alessandra Torresani for one episode and for the remainder of the series), the mayonegg-eating girlfriend of George Michael (), doesn’t leave much of an impression. At least not to ’s Bluth family. Our little Ann hog made the rounds with the Bluth boys, eventually hooking up with Gob (Will Arnett) for some reason. Nevertheless, we’re always happy to load Ann up in the car, whether we know she’s there or not. She’s really funny (we hope). [Matt Schimkowitz]

If you get to play a cute, helpful boyfriend—even if it’s for a short period of time and even if he’s a little bit whiny—it works. In , he plays Leo D’Amato, the Sheriff’s Deputy who briefly dates Veronica (Kristen Bell) in season one. Now, of course, VM fans know Veronica and Logan (Jason Dohring) were always going to be the endgame. ( ). But Leo was a pretty great “non-epic” respite, a gentler partner who kept recurring throughout the seasons. [Saloni Gajjar]

Here’s a hot take about : is easily one of the show’s top five best performers despite appearing only about a fifth of its episodes. She crushed it every single time in her role as Jan Levinson. She went from being the reasonable boss to a woman who eventually hooks up with and dates , and their ensuing relationship saw her turn her into quite an unhinged person, selling awful candles, and the like. Jan brings unexpected humor and chaos, whether it’s dancing to a song her assistant wrote or performing for her daughter in front of an audience. She’s the perfect crazy ex-girlfriend. [Saloni Gajjar]

You don’t expect to like Addison Montgomery () when she debuts in s season one finale with her icy demeanor, ready to break up Derek () and . Thankfully, with 19 long seasons under its belt, Grey’s gradually evolves Addison into one the franchise’s greatest characters. She’s fun, ambitious, vulnerable, and so easy to root for. She even got her very own six-season spin-off in Private Practice. Still, her appearances on the flagship series are the most rewarding. Any time Addison returns to Seattle Grace to help with a medical case is a good time. [Saloni Gajjar]

Is there a sadder recurring ex than Rickety Cricket (David Hornsby)? The guy isn’t even an ex; he’s a never was. He’s also the closest thing Dee’s got to one—as long as we don’t count Bill Ponderosa. After a lifetime of harboring a crush on Sweet Dee (Kaitlin Olson), Cricket’s downward spiral from the clergy to the gutter is well documented on It’s Always Sunny In Philadelphia, appearing each season with a new wound, injury, or infection. Sadder still, Dee often uses his undying and unrequited love for her against him, which leads to further emotional and physical harm. [Matt Schimkowitz]

Beeper King. Subway Hero. Coffee vending machine entrepreneur. ’s Dennis Duffy (Dean Winters) is a loser, and Liz Lemon (Tina Fey) knows it, but there’s an addictive comfort to having his specific type of chaos in her life. So what if he plays Halo under the name “Slut Banger”—he’ll still grab Liz a couple of cheeseburgers at the end of a long day and not care if she eats them in bed. But, like the TV shelf he set up in the corner of Liz’s living room, the comforting cheeseburger facade tends to come crashing down in spectacular fashion. Maybe he’s trying to re-enact a Balloon Boy scenario and frame himself as the hero. Maybe his cousin Teddy and his great Dane arrive uninvited for an indefinite stay in Liz’s apartment. Maybe he shows up on To Catch A Predator, even though he knew that girl was at least 22. Whatever it is, he’s never going to stick the landing—but god, the routine is entertaining to watch. [Jen Lennon]

Poor Ron Swanson ( has not one but two recurring exes haunting him throughout . And they’re both named Tammy. Tammy 1 (Patricia Clarkson) is cold and calculating, while Tammy 2 (played by ) is an endlessly chaotic honeypot who commits the extra unforgivable sin of being a “punk-ass book jockey,” a.k.a. a librarian. Eww. Unfortunately for Ron, it’s kind of hard not to root for his misery throughout the series because both are as delightful as they are absolutely terrifying. [Emma Keates]

Katherine Pierce (Nina Dobrev) is a menace, but oh what an amusing, incredibly funny, and hot menace she is. The build-up to her arrival during is intense—she’s the hyped-up ex of both Salvatore brothers, and they secretly still hold a candle for her deep down. Her arrival is nothing short of a jaw-dropper. And over the course of the series, Katherine’s existence often turns our protagonists’ lives upside down. She’s untrustworthy and selfish, but that’s what makes her the ideal, unforgettable villain for Dobrev played several roles in TVD, but her appearances as Katherine will always be the standout. (Sorry, Elena Gilbert!) [Saloni Gajjar]

is littered with notable exes of Mindy Lahiri (), as well as actors Kaling clearly enjoyed working with based on the fact that they’d return again and again. Perhaps the most memorable of these is Pastor Casey (Anders Holm), Mindy’s former fiancé and a preacher-turned-DJ. They were an on-again, off-again couple who couldn’t help rekindling their romance every time they reunited, managing to match each other for ridiculousness. A lot of great stars passed through The Mindy Project, but what made Casey the best ex was simply Holm’s commitment to the bit and the zany rapport he developed with Kaling. [Mary Kate Carr]

Before anyone raises eyebrows about Tariq’s inclusion in this list because is relatively new, let me ask: Have you seen Tariq? He may not have been a good boyfriend to (), but he knows how to chew the scenery whenever he shows up—and usually, it’s to do some kind of song-and-dance performance, which makes it even funnier. Here’s hoping he pops up a lot over Abbott’s sure-to-be-lengthy run. [Saloni Gajjar]