Against all odds, It’s Always Sunny in Philadelphia has grown into one of the most celebrated and longest-running television comedies of the modern era. Always Sunny has 14 seasons and over 150 episodes under their belt, with many more seasons still on the way. The odd, unrepentant comedy initially seemed like it wouldn’t find the audience to reach a second season, but now it’s become a flagship program of the FX Network.
The cynical attitude of the characters in It’s Always in Philadelphia has also influenced many other sitcoms that have come out of the 2000s. Always Sunny has an exceptional cast, but there have also been some surprising guest star cameos that have snuck in.
10 Josh Groban Pokes Fun At Himself In Dee’s Ultimate Fantasy
“The Gang Saves the Day” is the 100th episode of It’s Always Sunny in Philadelphia and the installment marks the milestone with a particularly playful entry. When presented with a convenience store robbery, each member of the group fantasizes over how they’d resolve the situation and the radical turns that their lives would take as a result.
Dee’s version of events sees her achieve fame, success, and snag musician Josh Groban as her husband (although she speedily divorces him for Brad Pitt). Groban is perfectly self-effacing and just praises Dee’s talents during the heightened fantasy.
9 Guillermo Del Toro Steps In As The Twisted Head Of The McPoyle Party
The main characters in Always Sunny already skew towards the weirder side of society, but the McPoyles are by far the strangest individuals within the series. Every new detail that comes to light about the McPoyle family is appropriately disturbing, but the patriarch of the clan, Pappy McPoyle, is introduced in "McPoyle vs. Ponderosa: The Trial of the Century."
Pappy McPoyle could qualify as the weirdest of the family, right down to his hermit attire and nearly feral attitude. All of this makes it even harder to believe that it's Oscar-winning director, Guillermo del Toro, in the role.
8 Sinbad Plays A Hallucinatory Version Of Himself That Plagues Dennis
Season four's "Dennis Reynolds: An Erotic Life" pushes most of the cast of It's Always Sunny out of their comfort zones, but Dennis is in an especially dire state after he ends up admitted into a questionable rehab facility.
While in rehab, Dennis bonds with eccentric versions of Sinbad and Matchbox 20's Rob Thomas. These cameos are so random, but that's exactly why they work so well and keep Dennis questioning the stability of his mental state. Sinbad really goes for broke in the performance and doesn't waste the opportunity to go big.
7 Christopher Lloyd Is One Of Charlie’s Very Worst Christmas Memories
The prospect of an It's Always Sunny Christmas special may immediately make some audiences squirm over the depraved depths that it will reach. "A Very Sunny Christmas" doesn't disappoint and it mixes Christmas cheer with the comedy's twisted sense of humor.
One of the centerpieces of the installment revolves around Charlie's lingering trauma over Santa, due to the excess of men dressed as St. Nick that would keep his mother company. One of the many fake Santas that visits Charlie's mom is Christopher Lloyd. It's fantastic to see Danny DeVito’s former Taxi co-star hiding in a silly fake beard.
6 David Benioff & D.B. Weiss Play Checked Out Gatekeepers In A Fun Nod
It's always a lot of fun when the teams behind different television shows can publicly share their adoration and respect for each other's works. David Benioff and D.B. Weiss, the showrunners behind HBO's Game of Thrones, are also major It's Always Sunny fans.
The duo actually scripted an episode of the series, "Flowers for Charlie," but they also briefly show up on-screen, too. "The Gang Goes to a Water Park" features the writing team as a pair of bored lifeguards, which shows that there's no lack of love between these two shows.
5 Dax Shepard’s Jojo Gets Swept Up By The Allure Of Cult Security
"Ass Kickers United: Mac and Charlie Join a Cult" is one of the more heightened episodes of It's Always Sunny and it benefits from juxtaposing Mac and Charlie against a group of new lost souls, some of which seem to be even more out of control than them.
One of the derelicts that join them in their cult efforts is Dax Shepard. He plays a construction worker named Jojo, but he does a great job to accentuate the character's unpredictable nature, which ultimately ends in self-immolation.
4 Retta Blends In As A Hapless Hardware Store Employee Who’s Had Enough
It's Always Sunny has been able to lampoon many of the different trends that television has embraced. Season four’s, "The Gang Gets Extreme: Home Makeover Edition," features the characters hopelessly out of their league when they only make their targets' homes become more inhospitable.
When the gang heads out to get supplies at a hardware store, they briefly make contact with Parks and Recreation's Retta as one of the store's employees. This cameo is thankless and pre-dates Parks and Rec by several years, which means it's likely more of a genuine role for Retta, but it pleasantly stands out now.
3 Tiffany Haddish Is Subjected To Frank’s Advances
The earliest episodes of It's Always Sunny represent the series' at its most crude and juvenile, but there are also some exceptional cameos that sneak by in their first few seasons. "Charlie Gets Crippled" kicks off the second season and it includes an extended sequence where Charlie and Frank celebrate their success at a strip club.
Tiffany Haddish shows up as "Stripper #3" and it's one of the bigger examples of a major star in a completely gratuitous role. This is another case where Haddish has not yet broken out as a star, but it gives the episode extra significance.
2 Alexandra Daddario’s Ruby Taft Promises Charlie A Happy Ending
One of the longest-running storylines in It's Always Sunny in Philadelphia is Charlie's obsessive, unrequited romantic feelings for the Waitress. Season eight's "Charlie and Dee Find Love" attempts to subvert this dynamic as it puts the Waitress into a vulnerable and wanting position after Charlie finds fulfillment.
HBO regular Alexandra Daddario is the perfect choice for Ruby Taft, Charlie's partner who puts up with his weird habits, but is ultimately too shallow for him. He leaves her behind in a huge display of power and self-reliance.
1 Keegan-Michael Key Is Forced To Rein In The Gang’s Chaos
"The Gang Goes on Family Fight" is an underrated episode from It's Always Sunny's tenth season that's ostensibly set entirely within an episode of the Family Feud knockoff, “Family Fight.” This turns into an excellent character showcase where the gang's nonsense only encourages further madness.
Talented comedian Keegan-Michael Key plays the host of “Family Fight” and while he's present throughout the whole entry, his character is intentionally low-key and meant to highlight everyone else's strangeness. Key knows how to properly disappear in the role and let the gang shine.
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