It’s Always Sunny in Philadelphia has spent 20 years as a highlight of the comedy world, with a massive number of big-name stars making an appearance at Paddy’s Pub. That extends to the show’s Season 17 premiere, which continues the crossover with Abbott Elementary and shifts the focus to the Gang and their antics. However, the cast of Abbott Elementary is far from the first stars to run afoul of Dennis, Dee, Mac, Charlie, and Frank.
Some of the best guest stars have matched the comic energy of the Gang, bringing their own unrestrained energy to the show. Others have played realistic or calm characters, naturally contrasting the extremes of the rest of the main cast. A few have even been genuinely emotional, delivering real human moments in a show mostly about awful people. Here are the best 10 guest stars in It’s Always Sunny in Philadelphia and where you can find their other movies and TV shows on apps like Apple TV+, Netflix, and Hulu!
Judy Greer
Season 3, Episode 5, "The Aluminum Monster vs. Fatty Magoo"
An early but memorable guest star in It’s Always Sunny in Philadelphia, Judy Greer was a great early addition to the universe of the darkly hilarious sitcom. Greer has been a fixture of the comedy world for years, with starring roles in shows like Archer and memorable supporting turns in films like 13 Going on 30.
Greer plays a uniquely straightforward character in It’s Always Sunny in Philadelphia, opposite a far more unstable Dee. An old friend of Dee who has risen up in the world, Greer’s Ingrid finds herself the target of Dee’s scorn and the rest of the Gang’s ambitions. Ingrid is a perfect counterbalance to Dee, a comically blunt but never condescending contrast to the comically awful Dee. It’s a bit of a departure for Greer, who specializes in playing her own brand of off-kilter behavior for comedy, but a memorable one.
Jason Sudeikis
Season 6, Episode 8, “The Gang Gets a New Member"
Season 6’s “The Gang Gets a New Member” played with the history of the Gang by introducing Schmitty, a member of the Gang who had been phased out years before the beginning of the show. Effectively a normal but sleezy guy who can’t help but poke fun at the absurd aspects of the Gang’s antics, Schmitty is played with casual charm by Jason Sudeikis.
Coming long before he’d be best known for playing the title role in the sweet Apple TV+ hit Ted Lasso, Sudeikis made a name for himself playing comedic dirtbags in films like We’re the Millers. Schmitty fits neatly into that mold while also having a unique enough perspective on the Gang that it subverts expectations in a clever manner.
Alexandra Daddario
Season 8, Episode 4, “Charlie and Dee Find Love”
One of the most surprisingly emotional supporting characters in the history of It’s Always Sunny in Philadelphia, Alexandra Daddario’s role as Ruby is a somber one when introduced as a new love interest for Charlie, drawing his attention away from the Waitress, Ruby Taft.
Daddario, who has also starred in searing dramas like True Detective and The White Lotus, gives a genuinely emotional performance that bounces perfectly off the constantly uncouth Charlie. This builds to the episode’s brutal final turn that lets Daddario use the full scope of her dramatic abilities to play against a shockingly villainous Charlie. It’s a moment that even catches the other members of the Gang by surprise and is one of the best unexpected plot twists in the show’s history.
Seann William Scott
Season 9, Episode 5, “Mac Day”
Season 9’s “Mac Day” is one of It’s Always Sunny in Philadelphia’s funniest episodes and an extended punch-line about the pathetic nature of the Gang’s self-proclaimed “badass bodyguard,” Mac. Serving as the perfect contrast to the blowhard and judgmental Mac is his laidback cousin, dubbed Country Mac. Played by American Pie and Dude, Where’s My Car? star Seann William Scott, Country Mac is everything the Gang could ever want, wrapped up in a calm, confident package.
The fact that Country Mac is then disposed of so unceremoniously is a darkly hilarious reminder that the Gang can never escape one another. Scott delivers one of the show’s best deadpan performances in the one-off appearance, making him one of the show’s best guest stars.
Keegan-Michael Key
Season 10, Episode 8, “The Gang Goes on Family Fight”
One of modern film and television’s best comedic actors, Keegan-Michael Key channels all of Steve Harvey’s frustrations into his game show host character in Season 10’s “The Gang Goes on Family Fight.” Grant Anderson is a typically cheery gameshow host who finds his patience quickly put to the test by the Gang. Their antics and bizarre answers quickly frustrate him, letting Key tap into the outbursts of rage that made his Luther character such a breakout hit on Key & Peele.
The episode largely focuses on the game show and the Gang’s inexplicable lead, which increasingly pushes all of Anderson’s buttons. One of the few guest stars to match the Gang’s chaotic energy with his own brand of absurd anger that he perfected on shows like Schmigadoon!, Keegan-Michael Key’s guest spot on It’s Always Sunny in Philadelphia is a hilariously unrelenting beat taken as far as it will go.
Guillermo del Toro
Season 11, Episode 7, “McPoyle vs. Ponderosa: The Trial of the Century”
One of cinema’s most prominent genre directors, Guillermo del Toro worked with Charlie Day on Pacific Rim before making a cameo appearance as Pappy McPoyle in Season 8. While this was a grimly hilarious beat, Pappy got a much more memorable (and hilarious) appearance in Season 11’s “McPoyle vs. Ponderosa: The Trial of the Century.”
Called to the stand during a trial between many of the show’s most consistent supporting characters, Pappy’s chaotic performance builds to a surprisingly (and hilariously) cartoonish turn when he unleashes his pet bird on the defense attorney. The director of films like Pan’s Labyrinth gets to go big on screen in a way he rarely does from behind the camera, and it’s a very funny appearance from one of modern Hollywood’s best filmmakers.
Mindy Kaling
Season 13, Episode 1, “The Gang Makes Paddy's Great Again”
Coming on the heels of Glenn Howerton seemingly leaving the show at the end of Season 12’s “Dennis’ Double Life,” the Season 13 premiere introduced The Mindy Project’s Mindy Kaling as a surprisingly great addition to the Gang. “The Gang Makes Paddy’s Great Again” deals with the fallout of Dennis’ departure to help raise the son he didn’t know he had, with Kaling’s Cindy taking his place as a major schemer of the group.
Kaling fits neatly into the dynamic of the group, utilizing them to the best of their strengths, even as the Gang’s flaws threaten to destabilize the work she’s put into her plans. As a one-off character who a returning Dennis quickly usurps, The Office star fits easily into the show’s sardonic style. Fans disappointed they didn’t get to see much of Dennis and Cindy going back and forth can check out Velma, which Howerton and Kaling co-starred in.
Dolph Lundgren
Season 14, Episode 2, “Thunder Gun 4: Maximum Cool”
Paying off a set up from seasons prior, Dolph Lundgren’s appearance in Season 14’s “Thunder Gun 4: Maximum Cool” is a very fun extended gag about the nature of the action genre. Established as one of the biggest action franchises in the It’s Always Sunny in Philadelphia universe, Thunder Gun’s latest movie gets a few clips shown in-universe as an example of an action franchise rebooting for a new generation.
The Rocky IV/Creed II star has a lot of fun poking fun at the kind of action movie roles he played in films like The Expendables and The Punisher, delivering some solid laughs throughout. Lundgren has always been a deceptively funny actor, especially in films like Tour de Pharmacy. It makes perfect sense to cast him as Thunder Gun for the episode. A minor but memorable payoff for Season 7’s “Thunder Gun Express,” Dolph Lundgren is a great pick to return.
Colm Meaney
Season 15, Episode 6, “The Gang's Still In Ireland”
One of the most surprisingly emotional guest stars in It’s Always Sunny in Philadelphia, Colm Meaney’s appearance in multiple episodes of Season 15 as Charlie’s biological father Shelley gives the show one of its best ever dramatic scenes. Portrayed as a well-meaning dope much in the same vein as his son, the Gangs of London and Hell on Wheels star brings a lovely grounded element to the character. The sweet rapport that grows between him and Charlie is undercut by the clear pain it causes Frank and the trauma that Charlie has to unpack, forcing typically non-stop joke machines to actually become humans.
Meaney makes Shelley a compelling character who never distracts from the actual focus of the story. Delivering a sweet performance that never stops being funny, Meaney brings some true weight to the show’s extended Ireland storyline.
Bryan Cranston and Aaron Paul
Season 16, Episode 5, “Celebrity Booze: The Ultimate Cash Grab”
One of the only times the guest stars in the episode were actively playing themselves, Bryan Cranston and Aaron Paul’s cameo in Season 16’s “Celebrity Booze: The Ultimate Cash Grab” stands out as one of It’s Always Sunny in Philadelphia’s most absurd episodes in a while. The episode reunites the Breaking Bad stars as the targets of the Gang’s newest scheme, by which they hope to get a celebrity endorsement for their newly concocted liquor.
The self-aware comedy picks up when it turns out the Gang only knows Cranston from Malcom in the Middle (and mistakes Paul for a grown Frankie Muniz), along with the discovery that their dynamic as Walter and Jesse have been flipped for these fictionalized versions of the actors. It’s one of the comedic highlights of Season 15, and one of the best celebrity cameos in It’s Always Sunny in Philadelphia.
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