It’s Always Sunny in Philadelphia has amassed a cult following since debuting in 2005, earning a place as one of the best comedy shows of the 21st century. The series follows the exploits of Charlie, Mac, Dennis, Dee, and Frank, co-owners of Paddy’s Pub who frequently engage in dangerous schemes no matter who gets hurt in the process. Currently airing its 16th season, the gang has not slowed down as they find new ways to embarrass themselves.
While the members of the gang are some of the funniest characters on television, It’s Always Sunny in Philadelphia is frequently bolstered by hilarious guest stars. Though the recent season has seen Bryan Cranston and Aaron Paul play themselves, often these guest stars play original characters that allow them to match the gang’s chaotic energy while drawing plenty of laughs.
10 “Rowdy” Roddy Piper as Da’ Maniac
“Rowdy” Roddy Piper was a legendary wrestler throughout the ’80s and ’90s, becoming one of the biggest stars to emerge from professional wrestling. Outside of wrestling he is best known for playing the lead role of Nada in John Carpenter‘s They Live, one of the greatest science-fiction movies of all time.
In Always Sunny, Piper played Da’ Maniac, a homeless wrestler who helps the gang when they decide to put on a wrestling event in “The Gang Wrestles for the Troops.” It is not often guest stars manage to be even wilder than the gang, but Piper excels as the unstable and dangerous Maniac, who may or may not have murdered his own children.
9 Jason Sudeikis as Schmitty
First gaining fame as a member of Saturday Night Live, Jason Sudeikis became one of the most recognizable comedy leading men of the 2010s, with some of Jason Sudeikis’ best movies including the likes of Horrible Bosses and We’re the Millers. He is best known for his portrayal of Ted Lasso, the kindhearted American who finds himself out of his depth when tasked with coaching an English soccer team.
Long before he took charge of AFC Richmond, Sudeikis guest-starred as Schmitty, a childhood friend of the gang who was kicked out after Charlie got jealous. Mac and Dennis decide to reunite with Schmitty in “The Gang Gets a New Member,” and he soon grows on their nerves. Sudeikis brings his trademark charm and humor to the role, and has a memorable second appearance in “The High School Reunion Part 2” where he draws Charlie’s ire one final time.
8 Seann William Scott as Country Mac
A staple of comedies in the 2000s, Seann William Scott is best known to audiences for his legendary role as Steve Stifler in American Pie, one of the best teen movies of the ’90s. While Stifler is an obnoxious and over-the-top sleazeball, his role as Country Mac in Always Sunny saw Scott adopting a more reflective and laid-back persona.
Appearing in “Mac Day,” Country Mac appears to be everything that Mac wishes he was: tough, wise, and comfortable with his gender identity, something that Mac was still struggling with at this stage. Always Sunny is a show stuffed with horrible people, but Country Mac stands as one of its most likable characters.
7 Sean “Diddy” Combs as Dr. Jinx
One of the biggest names in hip hop, Sean “Diddy” Combs built his career in the music industry throughout the ’90s and ‘2000s. While not normally an actor, Combs made a memorable appearance in the comedy Get Him to the Greek before his role in Always Sunny.
After the gang discovers “Charlie’s Mom Has Cancer,” they turn to Combs’ Dr. Jinx, who claims he can heal people through the power of plants and music. As the gang holds a fundraiser to raise Jinx’s $4200 asking price, he is outed as a fraud, revealed to be a church gardener in this amusing cameo.
6 Alexandra Daddario as Ruby Taft
First gaining fame for her role as Annabeth in the Percy Jackson movies, Alexandra Daddario has become one of the most popular actresses in Hollywood today. She has balanced supporting roles in highly-acclaimed series The White Lotus and True Detective with appearances in blockbuster movies like San Andreas.
Daddario appeared in Always Sunny as Ruby Taft, a young heiress who begins an unlikely romance with Charlie. Ruby is perhaps the kindest character to ever appear on the show, as she genuinely likes Charlie for he is, which makes his final cruel act one of the most irredeemable things he has ever done.
5 Josh Groban as Himself
Josh Groban has charted a career as a highly talented opera singer, releasing nine albums while making several appearances on Broadway. He has made a few acting appearances over the years, including the starring role in the Netflix crime-comedy The Good Cop.
Groban had been mentioned in Always Sunny before his guest appearance, with Dee being a fan of the singer. When she fantasizes what her life would be like as a famous actress in “The Gang Saves the Day,” she marries Groban, who is one of the few celebrities to play himself in the show. Their marriage lasts for 17 minutes, as Dee leaves him for Brad Pitt.
4 Keegan Michael-Key as Grant Anderson
Co-creator and star of the beloved sketch series Key and Peele, Keegan Michael-Key has built a reputation as a reliable comedic performer in both film and television. Famous for his high-energy delivery, Key found himself having to contend with the big personalities of the Always Sunny gang as they compete on a Family Feud-like show in “The Gang Goes on Family Fight.”
Key plays Grant Anderson, the host of the game show who does his best to hold it together as the gang’s wacky antics and bizarre answers threaten to derail the show. As the episode goes on Anderson begins to lose his composure as the gang wears him down, resulting in one of the funniest cameos in Always Sunny history.
3 Tom Sizemore as Trucker
The late Tom Sizemore built a career playing memorable supporting roles in legendary movies like Saving Private Ryan and Heat. Known for his grizzled demeanor, Sizemore used this persona to great effect when he guest-starred as a truck driver in the episode “The Gang Gets Stranded in the Woods.”
When the gang finds themselves in unfamiliar territory, the great outdoors, they each struggle with the situation in their own way. Charlie and Dennis decide to hitchhike with a passing trucker, who mistakes the men for a pair of sex workers. After driving to a hotel, Sizemore asks if they want to “slip into a room and split me open like a coconut,” prompting Charlie and Dennis to flee. It is a small but hilarious role, and remains a memorable cameo that is still quoted by fans.
2 Sinbad and Rob Thomas as Themselves
Best known for his stand-up comedy, Sinbad has appeared in several supporting roles throughout his career, such as in the family movies Good Burger and First Kid. Rob Thomas is the singer of the popular band Matchbox 20, and “Dennis Reynolds: An Erotic Life” sees the unlikely duo team up as they torment Dennis in a rehab facility.
Waking up in the facility with a hazy memory, Sinbad and Thomas play themselves as they threaten to beat Dennis and make him their b***h. Sinbad betrays his family-friendly image by playing an unstable bully who drops several great lines as the silent Thomas watches on with wide eyes, creating one of the greatest and most quotable cameos in Always Sunny history.
1 Guillermo del Toro as Pappy McPoyle
Guillermo del Toro is one of the most talented filmmakers of his generation, creating modern masterpieces like Pan’s Labyrinth and The Shape of Water. Despite not being an actor del Toro’s unlikely appearance in Always Sunny was born out of the friendship he formed with Charlie Day while making Pacific Rim together.
The inbred McPoyle family is a constant thorn in the gang’s side, and when they have to crash a McPoyle wedding, they encounter del Toro as Pappy McPoyle. The director is unrecognizable as the unhinged patriarch, ranting about eating his own babies before they eat him, before appearing again three seasons later during the McPoyle vs Ponderosa court case.
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