Now that we already know when every single episode in FXX’s 25-season (and one movie) marathon of The Simpsons is going to air, it’s time for us to start cherry-picking our favorites for the sake of not clogging our DVRs. While my colleague Josh has already touched on some of the most important episodes for any real die-hard Simpsons fan, I’m more interested in catching all of the best star-packed episodes that feature A- and B-list celebrity cameos, because it’s always fascinating to see how many famous people paid visits to Springfield over the years. Some have been frequent visitors while others were seen and then never heard from again, but the show was always at its best when the biggest celebrities brought their friends.
In fact, The Simpsons Movie (Aug. 29 at 6 PM ET) ended up having too many celebrity cameos, because appearances by Edward Norton, Minnie Driver, Isla Fisher and Erin Brockovich ultimately ended up on the cutting room floor, and even Kelsey Grammer’s Sideshow Bob contributions were left out, according to the film’s DVD commentary. Fortunately, the show’s individual episodes didn’t have to worry about axing famous voices for the sake of time, and the celebrity Simpsons cameo ended up becoming a staple of pop culture, like hosting Saturday Night Live or sleeping with Lindsay Lohan.
Longtime, devoted fans of the series obviously don’t need to be told that The Simpsons had a ton of celebrity guests along the way, but believe it or not there are people out there who have never watched an episode of this beloved show. Hell, I live with one. So consider this another cheat sheet for the fans who plan to set their DVRs accordingly come Thursday at 10 AM ET and a primer for any potential newcomers who want to dive in head first to catch their favorite celebrities in animated action.
Single Star Episodes of Note
As I mentioned, Josh has previously the most important episodes that every Simpsons fan should already be looking forward to, so I’m going to try hard not to repeat those by only including multiple-star episodes, but these solo celebrity appearances are favorites of mine that need inclusion:
Stark Raving Dad (Season 3, 1992) – Aug. 22, 3:30 AM ET
My friends and I used to meet before school on Monday mornings so we could talk about The Simpsons and In Living Color, and I still remember talking about this episode, because nobody ever thought that it was actually Michael Jackson playing Leon Kompowsky. After all, the credits showed that “John Jay Smith” provided the voice, but it was Jackson all along.
Bart’s Girlfriend (Season 6, 1994) – Aug. 23, 4:30 PM ET
Nancy Cartwright, who provides the voices of Bart Simpson, Nelson Muntz and Ralph Wiggum, among others, told a story about the time that Streep showed up to record her lines as Rev. Lovejoy’s daughter. Cartwright wanted the actress’s autograph was too shy and/or intimidated to ask because it was, you know, Meryl-f*cking-Streep, but when the day’s work was done, Streep asked Cartwright for her autograph because “her kids were great Simpson fans and she would be in big trouble if she did not get Cartwright’s autograph.”
Bart the Mother (Season 10, 1998) – Aug. 25, 4:30 PM ET
This was the final appearance of Phil Hartman and the retirement of Troy McClure. Hartman appeared on the show 52 times, more than any other celebrity to this day, and 25 times more than Joe “Fat Tony” Mantegna, who is in second place. I just don’t want this one to catch us all off guard when it airs, because I’m sad just thinking about it.
As for the celebritypaloozas…
Homer at the Bat (Season 3, 1992) – Aug. 22, 11:30 AM ET
As long as professional baseball exists, this episode will be mentioned among the sport’s most important contributions to popular culture, as Roger Clemens, Wade Boggs, Ken Griffey, Jr., Steve Sax, Ozzie Smith, José Canseco, Don Mattingly, Darryl Strawberry, and Mike Scioscia loaned their star power to the series and Mr. Burns’s softball team.
Krusty Gets Kancelled (Season 4, 1993) – Aug. 23, 2 AM ET
Entertainment icons like Johnny Carson, Hugh Hefner, Bette Midler, Elizabeth Taylor, Barry White, the Red Hot Chili Peppers, and even Luke Perry helped with Krusty the Clown’s comeback special. While most people think that it was just the illusion of animation, I like to believe that Carson actually lifted a Buick over his head.
Fear of Flying (Season 6, 1994) – Aug. 23, 6:30 PM ET
Not only did Anne Bancroft make an appearance as Marge’s therapist, tasked with erasing her titular fear of flying, but the stars of Cheers (Ted Danson, George Wendt, John Ratzenberger, Rhea Perlman, and Woody Harrelson) also reprised their iconic roles more than a year after the legendary NBC series ended. Ironically, Kelsey Grammer was the only actor who didn’t get to record lines, and he has voiced Sideshow Bob in 16 episodes.
Homerpalooza (Season 7, 1996) – Aug. 24, 2 PM ET
While Homer was busy taking cannon balls to his belly, Cypress Hill, Smashing Pumpkins, Sonic Youth, and Peter Frampton were working the stage for what stands as one of the greatest sitcom concert events since Jack Donaghy organized Kidney Now.
The Springfield Files (Season 8, 1997) – Aug. 24, 7 PM ET
David Duchovny and Gillian Anderson arrived in Springfield as Fox Mulder and Dana Scully, respectively, in one of the best TV crossover moments in history. If I made a Top 10 Simpsons Episodes of All-Time list, this would probably make the cut, if not for The X-Files, Chewbacca in a “Homer is a Dope” t-shirt and Jimbo trying to scalp Pearl Jam tickets from aliens, then at least for this moment:
The Last Temptation of Krust (Season 9, 1998) – Aug. 25, 10 AM ET
The allure of the episode is having standup comics like Jay Leno, Janeane Garofalo, Bobcat Goldthwait, Steven Wright, and Bruce Baum influence Krusty to become a dark, alternative comic who calls things the way he sees them and doesn’t pull punches for the sake of corporate coin. But the best part about it is his eventual selling out to the tune of Hank Williams, Jr. singing the most important commercial theme ever recorded.
Trash of the Titans (Season 9, 1998) – Aug. 25, 10 AM ET
Even without Homer getting his ass kicked at a U2 concert, Steve Martin is enough to make this episode noteworthy. But Homer getting his ass kicked at a U2 concert helps make it an amazing episode, because watching Homer suffer is one of the things that has made The Simpsons such a heartwarming and beautiful show.
When You Dish Upon a Star (Season 10, 1998) – Aug. 25, 5:30 PM ET
Homer befriended Alec Baldwin and Kim Basinger after accidentally parasailing into their summer home, because Lake Springfield is the ultimate destination for a married A-list couple that needs to escape the limelight. Ron Howard later steals Homer’s movie pitch for a time-traveling robot driving instructor, and sells it to Brian Glazer in one of the most realistic Simpsons moments ever written.
Sunday, Cruddy Sunday (Season 10, 1999) – Aug. 25, 9 PM ET
Fred Willard guest starred as Wally Kogen, a sucker who can’t say no to a sales pitch, and he and Homer led Springfield’s biggest football fans to Miami for the Super Bowl, where their tickets ended up being crackers. During the typical hijinks, they’re helped by Dolly Parton and run afoul of Rupert Murdoch. Troy Aikman, Dan Marino and Rosey Grier added some NFL star power, while John Madden and Pat Summerall closed out the episode with some analysis.
Kill the Alligator and Run (Season 11, 2000) – Aug. 26, 12 PM ET
First thing’s first, Robert Evans being in anything instantly makes it cooler, even if a Charlie Rose appearance is guaranteed to make me sleepy. But one of my favorite scenes in series history had Diedrich Bader’s sheriff asking Kid Rock’s cohort Joe C., “Would your mama want you stretching out that sweatshirt like that?” But overall, this is just a wonderful episode because it features Homer drunkenly delivering the most quotable Spring Break line ever: “Guess how many boobs I saw today, Marge… Fifteen!” Also, if someone calls you a bitch, the proper response is always: “Beeyotch? Moi?” A+ episode.
Tennis the Menace (Season 12, 2001) – Aug. 26, 7:30 PM ET
Like “Homer at the Bat,” this one featured an all-star cast of athletes, but it was only tennis so it wasn’t nearly as great. Andre Agassi, Pete Sampras and Venus and Serena Williams guest star as themselves in a story about classic family in-fighting. That’s a common Simpsons theme in case you need obviousness to punch you in the skull.
New Kids on the Blecch (Season 12, 2001) – Aug. 26, 8:30 PM ET
While Springfield’s children were being tricked into joining the Navy by Bart’s Party Posse’s subliminal messages, the bros from N Sync stopped by to give them pointers on being in a successful boy band. Even the animated version of Justin Timberlake had the worst hair of the 90s.
How I Spent My Strummer Vacation (Season 14, 2002) – Aug. 27, 12 PM ET
Homer is sent to Rock N Roll Summer Camp by his family after a series of events that never made much sense, but it allowed him to meet up with Mick Jagger, Lenny Kravitz, Tom Petty, Keith Richards, Brian Setzer, and Elvis Costello. As always, though, Homer learned an important lesson about family being above all else, and it resulted in violence against Principal Skinner, which is fantastic.
The Regina Monologues (Season 15, 2003) – Aug. 28, 12 AM ET
While this episode always felt like National Lampoon’s European Vacation on steroids, cameos by Tony Blair, Ian McKellen and J.K. Rowling are still pretty impressive. Also, the episode’s joke about England wanting the U.S. to take back Madonna is dead on, and Abbie Simpson is a character that deserved her own episode.
Homer and Ned’s Hail Mary Pass (Season 16, 2005) – Aug. 28, 1 PM ET
The next in a short line of sports superstar episodes, “Hail Mary Pass” featured LeBron James, Tom Brady, Michelle Kwan, Warren Sapp, and Yao Ming as themselves. Homer’s victory dance at a carnival inspired the athletes to raise their own bars in terms of excessive celebrations, and it all eventually leads to the most ridiculous Super Bowl halftime show ever conceived.
24 Minutes (Season 18, 2007) – Aug. 29, 5 PM ET
Kiefer Sutherland and Mary Lynn Rajskub appeared in this 24 crossover that impossibly makes “The Springfield Files” seem even greater than I remembered it. That’s not to say this wasn’t an entertaining episode, but it certainly didn’t give us anything resembling the awesomeness of Grandpa chasing a turtle that had taken his teeth.
O Brother, Where Bart Thou? (Season 21, 2009) – Aug. 30, 8 PM ET
For the record, the Smothers Brothers are way better than the Manning brothers, but from a starpower perspective, having Peyton, Eli and the third one who isn’t a Super Bowl-winning quarterback make cameos on an episode is pretty great.
Judge Me Tender (Season 21, 2010) – Aug. 31, 3:30 AM ET
Another crossover episode – ranking a distant third among the three that are listed here – this one starred American Idol‘s Simon Cowell, Randy Jackson, Ellen DeGeneres, Kara DioGuardi, and Ryan Seacrest, as well as Rupert Murdoch in his second Simpsons appearance. The positive aspect of this episode is that it’s Moe-centric, and bitter, cranky, ugly Moe is definitely one of the characters that never got old.
The Fight Before Christmas (Season 22, 2010) – Aug. 31, 7:30 AM ET
Martha Stewart helping us understand the true meaning of Christmas was sweet and all, but Katy Perry stole the episode in a live action performance with puppets, especially when she got inappropriately freaky with Moe. But as Moe so elegantly put it…
The Food Wife (Season 23, 2011) – Aug. 31, 5 PM ET
Anthony Bourdain, Gordon Ramsay, Mario Batali, and the Swedish Chef represented the greatest celebrity chefs known to man, but Tim Heidecker and Eric Wareheim are the most important guest stars of this episode. Actually, they’re probably ranked No. 2 behind the Swedish Chef, because he’s the best Muppet in the world.
Moonshine River (Season 24, 2012) – Sept. 1, 2 AM ET
Ken Burns narrated this episode that featured appearances by Zooey Deschanel, Sarah Michelle Gellar, Anne Hathaway, Natalie Portman, and Sarah Silverman as Bart’s past girlfriends. Like most episodes involving him, though, Cletus steals the spotlight because he’s amazing and wonderful, and I’d watch a spin-off series dedicated to him. Make it happen, Fox.
Steal This Episode (Season 25, 2014) – Sept. 1, 5 PM ET
Judd Apatow, Will Arnett, Leslie Mann, Seth Rogen, Paul Rudd, and Rob Halford all have roles in this episode about the problems with piracy, but none of them matters. Channing Tatum, son. Springfield’s dopest muthaf*cka all up in the yellow. Word.
