The 13 Best Romantic Guest Stars: Sitcom Edition

We were so thrilled with the recent news that Louis C.K. is returning to Parks and Recreation to rustle the recent reunion between Leslie (Amy Poehler) and Ben (Adam Scott) that we got to thinking. Louis C.K. was such a killer guest star on Parks — there have to be more of his kind. And once we started thinking about it, we realized there’s an overabundance of great romantic guest stars on our favorite sitcoms, which means we had to whittle it down to a few of our favorites. Maybe we’re not that great at whittling, because we’ve still got 12, but they’re all pretty unforgettable so I’m sure you’ll forgive us.

Louis C.K. Parks and RecLouis C.K. on Parks & Recreation

The comedian’s comedian stopped by Pawnee, Ind. for a few episodes to let his bumbling character, Dave, steal fair Leslie’s heart. While their romance almost hit the skids before it started thanks to that whole Madeline Albright/ Leslie’s grandma confusion, Louis C.K. eventually made a good impression by putting up with Leslie’s drunken late-night visit and her tireless tirade on the pre-teen bully/vandal/prankster/Bart Simpson wannabe, Greg Pikitis. Dave never really knew quite the right thing to say, but he was always earnest and sweet, and he made Leslie light up like a Christmas Tree. His return spells trouble for Beslie (is that what we call them?), but I’m still amped to see him come back.

matt damon 30 rockMatt Damon on 30 Rock

I struggled with choosing Michael Sheen or Matt Damon for this entry, but then I remembered the explosive breakup between Carol Burnett (Damon) and Liz (Tina Fey). Sorry, Wesley Snipes (Sheen), “Gangway for Footcycle” gets me everytime, but nothing beats a pilot’s discount at Sunglass hut. Damon was pitch perfect for Liz; from his name (a reference to Liz and Fey’s comedy heroine), to his constant references to mundane pilot perks that Liz would enjoy more than any other human, to his stalwart love for her show (which no one else in the world seems to give two cheesy blasters about), Carol is perfect for Liz…for a little while anyway. Eventually, they get points for the best breakup ever because they both hold up an entire plane in order for them to figure out they’re just too similar. Classic.

elizabeth banks 30 rockElizabeth Banks on 30 Rock

Just as Liz met her double in Carol, Jack (Alec Baldwin) met his match in Avery Jessup (Elizabeth Banks), the conservative financial reporter. Together, they worshipped Ronald Reagan, bought their daughter a saddle to ride the maid, and both shreiked with terror when their baby was not only born in CANADA, but with the help of socialized medicine. The horror. Avery too, had to say farewell, and in another dramatic way — she was kidnapped and taken to North Korea, never to be heard from again. This show sure knows how to get rid of a guest star, eh?

woody harrelson on will and graceWoody Harrelson on Will & Grace

I promise, I’m not trying to write about all NBC series, but man do they get great guest stars. You may remember that Connick Jr. was the yin to Grace’s (Debra Messing) yang as Dr. Leo Markus, but by far, her best boyfriend had to be the slovenly Nathan (Harrelson). As her neighbor, Nathan first drives her crazy, but of course hate turns to sexual tension and they end up together for a good chunk of Season 3. Of course, their breakup circumstances are pretty hilarious as well — they all stem from Nathan’s cry of “Marry me” during sex. They’re awkward around eachother until Grace decides that in order to fix it, she’ll propose to him. But he says no and breaks it off. Word to the wise: don’t propose marriage during bedroom activities.

luke wilson that 70s showLuke Wilson on That 70s Show

We thought nothing could come between Eric (Topher Grace) and Donna (Laura Prepon), but apparently all it takes is a Kelso. No, not Michael (Ashton Kutcher), but Casey Kelso the Trans-Am-driving charmer sure does the trick. He’s slimy and the complete anti-Eric, but he knows how to play the system and he’s old enough to drink beer. Swoon, amirite? He’s just as dumb as his younger brother, but he’s so charming, that Donna doesn’t seem to catch on until Bob orders Donna to stop dating him and Casey doesn’t seem to care. She wanted a laid-back dude, didn’t she?

tammy 2 parks and recMegan Mullally on Parks & Recreation

As Ron Swanson’s (Nick Offerman) second ex-wife, Tammy, Mullally draws on the already hilarious relationship with her real life husband (Offerman) to simultaneously terrify Ron and whip him into a disgustingly sexual frenzy. And her second appearance sees the craziest Ron we’ve ever witnessed, with cornrows, a boxing robe and a lack of mustache — from the friction. Shudder.

kristen bell party downKristen Bell on Party Down

If there’s anyone better to play a tiny, adorable, unbearably uptight girlfriend and catering manager, point me in their direction, but I think you’ll find that Kristen Bell is the tops. She played Uda, Henry Pollard’s (Adam Scott) girlfriend after fellow cater waiter Casey (Lizzy Caplan) breaks his heart. She’s terrifying, even when she’s not on screen, and her love of mundane things like The Mentalist are just the icing on the cake. Her proposal for Henry to give her a call for a date is one of the most haunting comedic moments in recent memory.

on Family Guy

Brian is obnoxiously pseudo-intellectual. He constantly assumes he’s so much smarter than every other person on the show, though he’s constantly shown to be completely pretentious. Nothing quite drives that point into the ground like his on-again-off-again girlfriend, Jillian. She was gorgeous, blonde and a complete and total idiot. She completely puffs up Brian’s confidence in that she’s so hot and that she constantly needs him to explain just about everything to her. “How do I know if I’m Jewish?” “Are you Jewish?” “Nope.” “There you go, sport.”