The 15 Best Guest Stars On The Simpsons, Ranked

"The Simpsons" has no shortage of memorable characters, but many of them are voiced by the same stable of actors who voice the main cast. Harry Shearer, Hank Azaria, and Dan Castellaneta are immensely talented voice actors, but sometimes, a role comes along that needs someone else to take the wheel. 

There are some common reasons why celebrities agree to guest star on "The Simpsons." But even if they're only doing it because their kids made them, they can still make an impact, even if their character is never seen again after a single appearance. Whether they were simply funny or profoundly affected a member of the main cast, these celebrity cameos weren't just gimmicks. They helped change the DNA of the sitcom.

/Film has already gone through the worst celebrity cameos "The Simpsons" has ever had. Now, let's look through the best of the best, ranking the greatest celebrity guest stars ever to grace Springfield.

Barry White had one of the smoothest, sexiest voices in all of music. Taking that voice and giving him lines where he's actively annoyed or disgusted with Springfield makes for utter hilarity. 

White appeared in season 4's "Whacking Day" as the special guest for the annual ceremony where Springfieldians beat snakes to death. White is told onstage what the event is really about, and he earns a spot on this list for no other reason than his reading of the line, "Oh God, no. You people make me sick!" It's a fantastic reversal of tone following him expressing his love toward everyone, and later in the episode, he sings "Can't Get Enough of Your Love, Babe" to drive the snakes to safety. 

It's a perfect example of a celebrity playing themselves. The episode doesn't revolve around White, but the plot is dependent on his presence since Bart and Lisa need the bass in his voice to get the snakes to their house. And most importantly, every line White says deserves a laugh.

"The Simpsons" got three out of four Beatles to guest star. Ringo Starr encouraged Marge to pursue her art, while Paul McCartney encouraged Lisa to continue down the path of vegetarianism. And then there's George Harrison, arguably the best Beatle cameo more so for how the episode treats him than anything he says. 

Season 5's "Homer's Barbershop Quartet" is a flashback episode to when Homer was a big music star. After winning a Grammy, Homer meets George Harrison at a party, but instead of being gobsmacked by the fact he's talking to a Beatle, he just wants to know where he got a brownie. Homer then proceeds to eat numerous brownies while Harrison looks on, and it's amazing. And in a brilliant nod to Fab Four lore, the ex-Beatle later deadpans, "It's been done," when Homer and his group, the Be Sharps, reunite for a rooftop concert at Moe's Tavern.

One major source of contention "Simpsons" fans have with modern episodes is how they glorify celebrities, like everyone in Springfield obsessing over Lady Gaga for an episode. These cameos work best when a celebrity's presence is used sparingly, and they're not showered with praise. Harrison is a Beatle, and Homer couldn't care less. That's a prime use of a celebrity cameo if there ever was one. 

Bruce Springsteen continually refuses to appear on "The Simpsons," but maybe he needs to reconsider seeing how so many singers have appeared on this list of the best "Simpsons" guest stars. Johnny Cash as Homer's spirit guide on "El Viaje Misterioso de Nuestro Jomer (The Mysterious Voyage of Homer)" is the latest, as he provides the necessary gravitas to help Homer realize Marge is his true soulmate.

After eating Guatemalan insanity peppers at a chili cook-off, Homer hallucinates a stunningly animated surrealist world. He meets the Space Coyote, who helps him reach his necessary revelation. Cash's voice brings a level of profundity to the proceedings, which makes the silly jokes land all the harder, like when he tells Homer he should get more possessions because he doesn't even own a computer or when he starts gnawing at Homer's ankle. 

The Space Coyote is one of those one-off characters who continue to resonate decades after their appearance. "Simpsons" creator Matt Groening even referred to Cash's cameo as "one of the greatest coups the show has ever had" in the season 8 DVD commentary. 

"The Simpsons" might be a wacky cartoon, but sometimes, less is more. Donald Sutherland as Hollis Hurlbut, the museum curator in "Lisa the Iconoclast," is a great example of that. He's not over-the-top; in fact, Sutherland played him fairly straight, almost as though a real-life human being was suddenly dropped into Springfield. But it's his eternal straight-man persona that makes the jokes land even harder.

Sutherland even ad-libbed Hurlbut's best line in the episode. After Lisa makes a joke about getting over Chester A. Arthritis, the curator laughs and says plainly, "You ... you had arthritis?" It's such an awkward line reading, but it works because it sounds exactly like how your parents would respond if you made a joke they didn't get.

Hurlbut's groundedness works in the story's favor, as he gets his own character arc in realizing Jebediah Springfield was a fraud after Lisa — who had become a pariah in Springfield by that point — shows him the proof. We only wish he would've shown up later throughout the series as an intellectual equal to Lisa, but no good thing can last. 

Homer has had a lot of would-be paramours over the years to test his relationship with Marge, but none have been as great as new co-worker Mindy Simmons, voiced by Michelle Pfeiffer, in season 5's "The Last Temptation of Homer." Not only is she beautiful, but she also loves donuts, beer, and taking naps at work. She's everything Homer could want in a woman, and Pfeiffer brings her to life wonderfully. 

It's hilarious to hear Pfeiffer's sultry voice mimic Homer's mannerisms, like when they both say, "Mmmm ... foot-long chili dog." But there's a real vulnerability there too. She doesn't make her feelings toward Homer a secret but puts the decision in his court as far as what he wants to do. She wasn't the first woman to tempt Homer nor would she be the last. But no one has managed to come close to making the audience feel like another woman was truly perfect for Homer had he never met Marge. 

Danny DeVito brings an everyman charm to Homer's half-brother, Herb Powell, throughout his various "Simpsons" appearances. The first one came in season 2's "Oh Brother, Where Art Thou?" where he's a successful businessman who loses his fortune after seeking Homer's input on a new car. He gets his wealth back in season 3's "Brother, Can You Spare Two Dimes?" because it would've been a little sad for Homer to absolutely ruin another man's life. 

DeVito's Herb is another character who blends in seamlessly with the Simpson family. He's effectively a Bizarro version of Homer and a vision of what he could've been had he been raised a little differently. And he's a constant reminder that the world of this sitcom is far larger than most people realize. Herb even came back for the season 36 premiere "Bart's Birthday" to remind him of all the colorful characters he's met while he's still only 10 years old.

Patrick Stewart is no stranger to voice acting, with regular appearances on the likes of "Family Guy" and "American Dad!" But way back in season 6 of "The Simpsons," he took on the glorious role of Number One in "Homer the Great," an episode about Homer joining and then becoming the exalted chosen one of a secret fraternal organization. Number One oversees the group's duties, with Stewart lending his iconic voice to such low-brow lines like, "Now let's all get drunk and play ping-pong!"

Number One is truly one of the best one-off characters on "The Simpsons" because there's so much majesty to him. If Hollis Hurlbut represents the groundedness in Springfield, then Number One is everything ridiculous. The fact there's this all-powerful figure keeping aliens under wraps within Springfield is amusing to ponder. Number One may not have been seen again, but Stewart would return as "Vigorous Older Man" in the season 24 episode, "The Fabulous Faker Boy." To us, though, he will always be the regal Number One. 

While this list is a ranking of the best "Simpsons" guest stars, everyone is obviously entitled to their own opinions of what's "best." However, it's hard to argue that John Waters' appearance as John in season 8's "Homer's Phobia" is one of the most important guest spots in the show's history. 

The Simpson family befriends collectibles shop owner John, whom Homer likes until he realizes he's gay. This causes Homer to worry that John could turn Bart gay, and he goes to extreme lengths to prevent that. Some lines and jokes maybe haven't aged well, but it's great to see how "The Simpsons" dismantled the groomer narrative surrounding the gay community back in the 1990s. In fact, it's Homer who's effectively "grooming" Bart to adhere to toxic ideas of what a man is supposed to be, but John shows that, gay or not, there are plenty of ways to be comfortable in one's skin. 

Homer espouses some bigoted views, but the episode always makes clear that Homer is in the wrong for thinking those things. John's just a guy, and Waters brings humor and heart to him. 

No character has ever helped flesh Homer out as a character more than his mother, Mona Simpson, voiced by Glenn Close. She first appears in season 7's "Mother Simpson," and up until that point, we had seen bits and pieces of her. But for the most part, audiences just kind of assumed she had died. It turns out she's alive and simply on the run from authorities for her activism, but when she returns, she forces Homer to reconcile with a piece of himself that's always been missing. 

With Mona's return, one can't help but wonder how Homer would've turned out had she been around to raise him better. "Mother Simpson" jokes about how Homer has been trying to fill a hole in his heart with alcohol due to her absence, but that's kind of a good point to bring up. And while Homer screws up plenty in raising his own kids, he always tries to do what's right by them; perhaps that's his attempt to make sure they never feel like he did after his mom left him. 

With Close's superb voice acting, one really feels the warmth between the two. It's no wonder that even though Mona has passed away in the show's continuity in season 19's "Mona Leaves-a", she's continued to appear in flashbacks and other types of visions since.

Dustin Hoffman was one of the first big stars to lend his voice to "The Simpsons." He appears in season 2's "Lisa's Substitute" as the titular substitute teacher, Mr. Bergstrom. He's a kind, caring soul, someone on Lisa's intellectual level who takes a real interest in her gifts. He's the complete foil to Homer, who would rather watch football than go to a museum, and Hoffman brings a real emotional depth to the character, allowing the show to explore more serious themes rather than solely focusing on jokes every minute. 

Hoffman wasn't credited for his role on "Lisa's Substitute," instead being listed as "Sam Etic," a pun on "Semitic." Some have speculated this is due to Hoffman, a serious actor, not wanting to be affiliated with a cartoon, but if anything, his performance lends credence to the idea that voice acting is every bit as powerful as visual acting. In just one episode, viewers could feel Mr. Bergstrom instilling in Lisa a new sense of self, and that's worth celebrating.

If you're like me, you probably realized far later in life than necessary that Jessica Lovejoy is voiced by Meryl Streep. It's a testament to her abilities as a performer that she's unrecognizable, as opposed to many other celebrities who have appeared on the show who make their character, even if it's a child, just sound like themselves. 

In season 6's "Bart's Girlfriend," Bart develops a crush on Reverend Lovejoy's daughter, trying to turn himself into a good kid to impress her. However, he soon learns that she's even more rebellious than he is, and it's here where Streep really shines. The actor gives Jessica a devil-may-care attitude where she'll softly coo to Bart to get him to do whatever she wants. Some of her lines are downright devious, like after everyone blames Bart for stealing the church collection plate even though she did it; to this, she says, "If you tell, no one will believe you." 

Not only is Jessica a great character, but she also helps flesh out Bart's character, showing how even he has his limits. Hopefully one day, he finds a girl who allows him to be the petty thug he wants to stay as.

Albert Brooks has long been a secret weapon on "The Simpsons." He's voiced a vast array of characters to great effect. He's beguiling as bowling instructor Jacques trying to seduce Marge in "Life on the Fast Lane," and he's utterly nasty as EPA administrator Russ Cargill in "The Simpsons Movie." There's a certain chaotic energy to all of these roles Brooks excels at, but for the purposes of this list, let's focus on his greatest "Simpsons" role to date — Homer's new boss Hank Scorpio in season 8's "You Only Move Twice."

Scorpio has nonstop amazing lines, like his hammock monologue and, of course, "Ever seen a guy say goodbye to a shoe?" And while he's an evil mastermind, he's always an incredibly supportive boss to Homer, even encouraging him to quit his job and return to Springfield when it's clear his family isn't happy.

Given Scorpio's popularity, it's easy to see why "The Simpsons Movie" writers considered bringing him back as the villain instead of Cargill. Scorpio works so well because he's a one-and-done character who remains one of the best additions to the show all these decades later. 

Sheldon Leonard was reportedly first considered to voice Fat Tony on "The Simpsons," but he was unavailable, so the team opted for Joe Mantegna. While I'm sure Leonard would've done an admirable job, it's hard to envision anyone else voicing the character for so long. He may have first appeared on season 3's "Bart the Murderer," but he's become integral to Springfield's DNA ever since. 

He frequently shows up as a way to raise the stakes, like when Homer hires him and his goons to help Marge's struggling pretzel business in season 8's "The Twisted World of Marge Simpson." His gruff, raspy voice offers the aesthetic that he's a serious threat, but then the writers give him great lines like "You have 24 hours to give us our money, and to show you we're serious ... you have 12 hours" that are so ridiculous for someone as intimidating as him to say. 

Fat Tony easily could've been a one-off character on "Bart the Murderer." The episode was basically just an excuse to riff off gangster movies anyway, which didn't necessarily need to be a recurring thing. But having the mob frequently appear in Springfield is a fun motif.

Some celebrity guest spots on "The Simpsons" are just fine as one-offs. But others seem primed for recurring roles, and Sideshow Bob, voiced by Kelsey Grammer, has had his share of excellent appearances throughout the show's run. 

The best Sideshow Bob episodes see him at his most nefarious, such as his first main role in season 1's "Krusty Gets Busted" where he frames Krusty the Clown for armed robbery. It's hilarious to see him continue to crop up when he gets out of prison and engage in more schemes to kill Bart or to strike it rich somehow. The culmination of Sideshow Bob's greatness is easily season 5's "Cape Feare" where every bit involving him is glorious, from continuously stepping on rakes to explaining what "Die, Bart, Die" means. Grammer's voice acting is always on point, offering a worthwhile adversary to Bart and the rest of Springfield.

Sideshow Bob can easily show his deviousness in various ways. For instance, he can be a Republican mayor with all the fear-mongering that entails, or a representation of a high-brow snob who believes TV is worthless, much to the dismay of Bart and Krusty. Grammer brings a more intellectual type of villainy to Springfield, and no one could pull off this kind of character other than him. 

Phil Hartman appeared on 52 episodes of "The Simpsons," and every time, his role was a joy to watch. You might remember him from voicing washed-up actor Troy McClure, frequently narrating educational videos before getting his own spotlight in "A Fish Called Selma" where he marries Marge's sister. Hartman even wanted to make a live-action movie based on McClure that sadly never came to fruition following his death in 1998. 

Then there's Lionel Hutz, the incompetent lawyer the Simpsons keep hiring. And that's nothing to say of all the one-off characters Hartman took on, most notably unscrupulous businessman Lyle Lanley in season 4's "Marge vs. the Monorail." Hartman simply brought an infectious energy to any character he played, infusing any line with hilarity. 

Everyone has their own point for when the golden era of "The Simpsons" ended. For me, it ended after Hartman's characters were retired following his tragic death. A certain energy was lost once McClure and Hutz left Springfield for good, but at least we'll always have his episodes to remember him.