The Ultimate Ranking of Guest Stars in It's Always Sunny In Philadelphia

It's Always Sunny in Philadelphia, a long-running series, has captivated audiences for almost two decades with its unlikeable lead characters who run Paddy's Pub. However, the show's true gems lie in its guest stars who have managed to steal the spotlight. Despite 15 seasons, the formula of It's Always Sunny in Philadelphia has remained successful by maintaining its core theme of backstabbing for personal gain among a group of so-called best friends and co-owners of Paddy's Pub.

While the main cast, consisting of Glenn Howerton as Dennis, Charlie Day as Charlie, Rob McElhenney as Mac, and Danny DeVito as Frank, is undeniably outstanding, the guest stars on It's Always Sunny in Philadelphia have brought some of the most endearing characters to life. These self-absorbed friends and family members who run an Irish pub in South Philadelphia often play second fiddle to renowned actors making guest appearances. Some guest stars have even reprised their roles multiple times due to the exceptional appeal of their characters. However, there have been instances where fans felt certain guest appearances were unnecessary. Nonetheless, the series remains fresh and vibrant through its multitude of remarkable guest stars, elevating them to iconic status.

23 Retta

Retta, best known for her role as Donna Meagle in Parks and Recreation, made a brief appearance in It's Always Sunny's season 4, episode 12 titled "The Gang Gets Extreme: Home Makeover Edition." In this episode, Retta portrays the clerk at the hardware store where the gang goes to gather supplies. Like many other guest stars, Retta's role is a straight one, having to endure Charlie's ridiculous ideas. While enjoyable for Parks and Recreation fans, her character lacks substantial material to work with.

22 Brian Huskey

"2020: A Year in Review"

Brian Huskey stars in season 15, episode 1 of It's Always Sunny in Philadelphia, titled "2020: A Year in Review." This particular episode stands out for its unique concept, cleverly incorporating the numerous catastrophic events of 2020 and suggesting that the gang played a prominent role in each one. The storyline unfolds when Gary (played by Brian Huskey) conducts an audit of the gang after the owners of Paddy's Pub fail to repay several PPP loans. Huskey's reactions to the gang's tales are absolutely priceless. While Huskey made an appearance in Ant-Man, he is most well-known for his distinctive voice, having lent his talents to various characters on Bob's Burgers.

21 David Huddleston

"

A Very Sunny Christmas"

Fans were left in a frenzy when the creators of the show introduced the other Lebowski character from The Big Lebowski (Huddleston also had a role as one of the Johnston brothers in Blazing Saddles). Huddleston gained immense popularity for his portrayal of the billionaire in the Coen brothers' cult classic film, where he was mistaken for the Dude, and his appearance in It's Always Sunny in Philadelphia possibly became his second most recognizable role. This comedy icon took on the character of Frank's former business partner in the exclusive DVD special, "A Very Sunny Christmas," where he played a significant part in one of the gang's absurd schemes. In the special, he hilariously attempts to convince Frank that he is a ghost before ultimately threatening to kill him.

20 Pablo Schreiber

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"A Very Sunny Christmas" featured Pablo Schreiber, best known for his role as George Mendez in Orange Is The New Black. Mendez, also known as "Pornstache," was a character notorious for his creepy behavior. However, Schreiber showcased a less creepy side in his appearance on It's Always Sunny. He portrayed Ricky Falcone, a man whose stolen toy robot by Mac on Christmas was a central plot point in the episode. Decades later, Mac felt guilty and decided to return the toy. However, instead of making Eddie's life better, Mac actually made it worse and even bullied him about his depressed lifestyle. Despite being one of the earlier episodes, Schreiber's character was not fully utilized and remains one of the most overlooked guest stars on It's Always Sunny.

19 Rob Thomas

The appearance of singer Rob Thomas in season 4, episode 9 of "It's Always Sunny" titled "Dennis Reynolds: An Erotic Life" is a memorable and unusual casting choice. Despite being known as a musician rather than an actor, Thomas' role in the episode aligns with Dennis' hallucinations and paranoia. It turns out that Thomas landed the gig after inviting the cast of "It's Always Sunny" to one of his concerts, which ultimately led to him being offered a part on the show.

18 Sinbad

"Dennis Reynolds: A Tale of Sensuality"

While Rob Thomas may be considered one of the most eccentric guest stars on It's Always Sunny, it is even more peculiar to discover who shared the screen with him. Joining Thomas was comedian and actor Sinbad, renowned for his comedic performance as Myron Larabee in the beloved holiday film Jingle All the Way starring Arnold Schwarzenegger. In this particular episode, both Thomas and Sinbad portray patients at a mental institution who relentlessly pester Dennis. Adding a touch of humor, Sinbad consistently reminds everyone of Thomas' stature as the lead vocalist of Matchbox 20.

17 Geoffrey Owens

Geoffrey Owens, a notable recurring guest star on It's Always Sunny, brings intrigue with his appearances in the episodes "Frank's Pretty Woman," "The Gang Gets Invincible," and "The Gang Makes Lethal Weapon 7." In each of these instances, Owens portrays an actor who is hired by the gang. His roles include impersonating "Fake Tiger Woods," "Fake Donovan McNabb," and "Fake Don Cheadle" as part of various schemes. Owens's deadpan demeanor and apparent indifference to his surroundings, seemingly motivated solely by his paycheck, add an extra layer of comedy to his performances. While it remains uncertain, there is a possibility that Owens may actually be playing himself, as Mac and Dennis make references to his previous role in The Cosby Show, aligning with Owens's real-life portrayal of Elvin on the sitcom.

16 Dax Shepard

Dax Shepard, known for his roles as Frito Pendejo in Idiocracy and Vince in Employee of the Month, takes on his strangest character yet in his filmography. As a guest star on It's Always Sunny, Shepard makes a cameo appearance in season 10, episode 10, titled "Ass Kickers United: Mac and Charlie Join a Cult." In this episode, he becomes one of Charlie and Mac's devoted followers. Shepard's talent for portraying foolish characters shines through in his role as a cult member who dutifully adorns his face with stickers.

15 Dennis Haskins

Charlie Got Molested is an episode from the first season of It's Always Sunny in Philadelphia, featuring Dennis Haskins as Mr. Belding, the beloved principal from Saved By the Bell. In this episode, Haskins portrays the gang's former teacher, who is falsely accused of child molestation. Mac, feeling jealous, tries to seduce the teacher by wearing his old gym shorts. Interestingly, Haskins' former co-star Patrick Thomas O'Brien also appears as a teacher in another episode of It's Always Sunny in Philadelphia, titled "The Gang Runs For Office," from the show's second season.

14 Christopher Lloyd

"

A Very Sunny Christmas"

Christopher Lloyd, an iconic figure of the '80s who gained fame through his roles in Back to the Future, Clue, Who Framed Roger Rabbit?, and most recently, his inclusion in season 3 of Mandalorian, delivers one of the most memorable cameo appearances among all the guest stars in It's Always Sunny. Even ardent Back to the Future fans fail to recognize him, adding to the irony. While he remains hidden, it is worth noting that Lloyd is the most recognizable actor with an incredibly prolific career among all the stellar Always Sunny guest stars. In the "Always Sunny Christmas Special," the actor conceals himself behind a white Santa beard. In a flashback, he pays a visit to Charlie's mother during the festive season, triggering a violent reaction from Charlie when he realizes the true identity of Santa Claus.

13 Josh Groban

"Mac's Mon Burns Down Her House"

Josh Groban not only excels as a musician, but he also showcased his impressive comedic skills in season 6, episode 6, "Mac's Mon Burns Down Her House". Playing the role of Dee's short-lived boyfriend, Groban left a lasting impression. However, his character was overshadowed when Dee had a daydream about being with Brad Pitt, leading to their breakup. Despite the show's occasional emphasis on musical elements, Groban's talents were not fully utilized in this particular sequence. It is a missed opportunity considering how eagerly fans have been anticipating a Nightman sequel, a much-desired follow-up episode.

12 Keegan-Michael Key

"The Gang Goes on Family Fight"

11 Alexandra Daddario

: The Paddy's Pub gang once found themselves on a game show called Family Fight, clearly inspired by Family Feud. This hilarious occurrence took place in season 10, episode 8 of It's Always Sunny in Philadelphia titled "The Gang Goes on Family Fight." To make things even more entertaining, Keegan-Michael Key was invited to play the role of the host. Interacting with the gang, Key's portrayal of Steve Harvey and his mocking of the Paddy's Pub crew solidified him as one of the top guest stars on the show.

"Charlie and Dee Find Love"

10 Stephen Collins

Alexandra Daddario's role in It's Always Sunny in Philadelphia surpasses the typical guest star appearance. Even though she wasn't widely known at the time she appeared in season 4, episode 8, "Charlie and Dee Find Love," her screen presence was undeniable. Prior to gaining recognition in the 2017 Baywatch remake and portraying Rachel Patton in The White Lotus, Daddario briefly portrayed Charlie’s love interest. Till this day, Daddario's character Ruby Taft remains the only woman who has managed to divert Charlie's attention from his infatuation with the waitress.

"Dennis and Dee Get a New Dad," "Dennis and Dee's Mom Is Dead"

Stephen Collins gained fame for his portrayal as the Reverend and father of seven in the TV series 7th Heaven. It is rather ironic that he took on the role of the biological father of Dee and Dennis in It's Always Sunny in Philadelphia, considering its explicit content. In the season two finale, Collins was introduced as their biological father, and he cunningly outsmarted Dee and Frank when they attempted to deceive him. Initially, Dee and Dennis were influenced by his seemingly virtuous character, but soon they realized that such a lifestyle was not suited for them. This guest appearance by Collins is widely regarded as one of the highlights in the history of It's Always Sunny.

9 Jason Sudeikis

"The Gang Gets A New Member"

Jason Sudeikis portrayed the character of Schmitty in the eighth episode of the sixth season titled "The Gang Gets A New Member" in the TV show. His arrival was cleverly hinted at earlier in the series, starting with a mention in the third episode of the third season titled "Dennis and Dee’s Mom Is Dead." However, it was not until the sixth season that viewers got to see him on screen. Sudeikis reprised his role as Schmitty once again in the thirteenth episode of the seventh season called "The High School Reunion, Part 2." His portrayal of the charmingly irritating Schmitty is one of the most memorable guest appearances in It's Always Sunny. This is noteworthy as Sudeikis has gained immense popularity as a television actor, largely thanks to the success of his show Ted Lasso. Furthermore, he also co-starred with Charlie Day in the film Horrible Bosses.

8 Oscar Nunez

“The Gang Tries Desperately to Win An Award"

7 Guillermo Del Toro

: Oscar Nunez, known for his iconic role as Oscar in The Office, demonstrates his TV sitcom royalty once again. Making a cameo appearance in season 9, episode 3 titled "The Gang Tries Desperately to Win An Award," Nunez takes on the role of the Sudz Manager. As the gang attempts to revitalize the bar's customer service, which had been neglected for years, Paddy's Pub ironically manages to further tarnish its reputation. Nunez skillfully embodies the character he has been recognized for over the past two decades—a clean-cut, by-the-book persona—creating a seamless crossover between sitcoms. It's almost as if The Office's Oscar has seamlessly transitioned into the role of a bar manager.

"The Maureen Ponderosa Wedding Massacre."

6 Sean “P. Diddy” Combs

Guillermo del Toro, known for directing dark horror fantasy movies such as Pan's Labyrinth and Hellboy, makes a memorable appearance in the It's Always Sunny in Philadelphia episode titled "The Maureen Ponderosa Wedding Massacre" from season 8. In this horror parody, del Toro portrays the character Pappy McPoyle as the gang unintentionally intrudes on a wedding. Initially regarded as a crazy individual due to his tendency to ramble incoherently, Pappy tries to warn the group about an impending zombie invasion. However, his credibility is only established when the zombies actually emerge.

"Charlie's Mom Has Cancer"

5 Judy Greer

is one of the greatest guest stars to ever appear on It's Always Sunny in Philadelphia. In season 8, episode 6, titled "Charlie's Mom Has Cancer," he portrayed the eccentric character Dr. Jinx. This yellow-jumpsuit-wearing doctor operated his practice from his garage. Even though the gang hired him to assist Charlie's mom in her battle against cancer, many viewers were skeptical of his qualifications. Despite this, Combs has established himself as a remarkably talented comedy actor, particularly with his performance as the strict record label owner in Get Him to the Greek.

"The Aluminum Monster vs. Fatty Magoo"

Judy Greer is widely recognized for her distinctive face on television, having appeared in numerous shows. While she is most famous for her portrayal of Kitty Sanchez in Arrested Development, she has also made appearances on Californication, Royal Pains, Modern Family, House MD, ER, and Two and a Half Men. In "The Aluminum Monster vs. Fatty Magoo," the fifth episode of season 3 of It's Always Sunny in Philadelphia, Greer plays Ingrid, a social outcast from Dee's high school days. As expected, tension arises between them when Dee realizes Ingrid has achieved greater success, making Greer one of the standout guest stars on the show.

4 Dolph Lundgren

"Thunder Gun 4: Maximum Cool"

Movie star Dolph Lundgren's guest appearance on It's Always Sunny hilariously embraces his past as an action hero in macho movies. In season 14, episode "Thunder Gun 4: Maximum Cool," the gang eagerly attends a test screening of the highly anticipated Thunder Gun movie franchise, which has been a recurring topic on the show. Surprisingly, this is the first time that viewers are treated to actual clips of a Thunder Gun film, with Lundgren perfectly embodying the role of Thunder Gun. Lundgren's portrayal is a brilliant stunt casting choice that showcases his expertise in the genre, making him one of the standout guest stars on It's Always Sunny.