#19. Season 23 (2011–2012)
Every Guest Star: Tom Colicchio, Kiefer Sutherland, Jackie Mason, Aron Ralston, Jane Lynch, Gordon Ramsay, Mario Batali, Anthony Bourdain, Tim Heidecker, Eric Wareheim, Andy Garcia, Neil Gaiman, John Slattery, Matthew Weiner, Kevin Dillon, Janeane Garofalo, Jackie Mason, Joan Rivers, Ted Nugent, Dana Gould, Armie Hammer, David Letterman, Jeremy Irons, Michael Cera, Jamie Hyneman, Adam Savage, Julian Assange, Allison Krauss and Union Station, Jackie Mason, Shepard Fairey, Ron English, Kenny Scharf, Robbie Conal, Glenn Close, David Byrne, Brent Spiner, Treat Williams, Steve Coogan, Bryan Cranston, Eric Idle, and Lady Gaga.
Best Episode: “The Book Job”
Most Emblematic Episode of the Season As a Whole: “The Book Job,” because the satirical “The Book Job” and the sweet “Holidays of Future Passed” are two modern-day Simpsons classics that single-handedly elevate season 23 over its fellow twenty-something peers. Negative points for the 43,583 guest stars, through.
#18. Season 19 (2007–2008)
Every Guest Star: Stephen Colbert, Lionel Richie, Maya Rudolph, Plácido Domingo, Matt Dillon, Steve Buscemi, Ted Nugent, Julia Louis-Dreyfus, Alan Moore, Art Spiegelman, Dan Clowes, Jack Black, David Hyde Pierce, John Mahoney, Keith Olbermann, Jon Stewart, Dan Rather, Kurt Loder, Weird Al, Topher Grace, Terry Gross, Beverly D’Angelo, the Dixie Chicks, Zooey Deschanel, Jim Jarmusch, John C. Reilly, Glenn Close, Lance Armstrong, and Drew Carey
Best Episode: “Eternal Moonshine of the Simpson Mind”
Most Emblematic Episode of the Season As a Whole: “That ’90s Show,” because if you want to watch two Simpsons fans fight, ask them what they think of “That ’90s Show.” The continuity makes no sense, it relies on far too many 1990s references, and Homer is a Cobain-like grunge idol for some reason, but goddamn if “he who is tired of Weird Al is tired of life” doesn’t make me laugh. That’s typical of the season as a whole: funny moments in otherwise lackluster episodes, except for the great “Eternal Moonshine of the Simpson Mind.”
#17. Season 17 (2005–2006)
Every Guest Star: Alec Baldwin, Terry Bradshaw, Dennis Rodman, Lily Tomlin, Maria Grazia Cucinotta, Michael York, William H. Macy, Joe Frazier, Susan Sarandon, Antonio Fargas, Dave Thomas, Randy Johnson, Ricky Gervais, Richard Dean Anderson, Frances McDormand, Sal Bando, Gene Tenace, Melanie Griffith, Larry Hagman, Mandy Moore, and Stacy Keach.
Best Episode: “My Fair Laddy”
Most Emblematic Episode of the Season As a Whole: “We’re on the Road to D’ohwhere,” because it’s right in the middle of The Simpsons most middle-of-the-road season. Not bad, not good, just…there.
#16. Season 18 (2006–2007)
Every Guest Star: Joe Pantoliano, Michael Imperioli, Metallica, the White Stripes, Phil McGraw, Richard Lewis, Fran Drescher, Sir Mix-a-lot, Kiefer Sutherland, Tom Wolfe, Gore Vidal, Michael Chabon, Jonathan Franzen, J.K. Simmons, Elvis Stojko, Sab Shimono, Natalie Portman, Eric Idle, Peter Bogdanovich, Andy Dick, James Patterson, Meg Ryan, Stephen Sondheim, Jane Kaczmarek, J.K. Simmons, Betty White, Jon Lovitz, Ronaldo, Stephen Hawking, Kiefer Sutherland, Mary Lynn Rajskub, and Ludacris.
Best Episode: “Moe’N'a Lisa”
Most Emblematic Episode of the Season As a Whole: “Rome-old and Juli-eh,” because the instance someone decided that Grampa should fall in love with Selma, “They’ll Never Stop The Simpsons” became prophetic.
#15. Season 14 (2002–2003)
Every Guest Star: Mick Jagger, Keith Richards, Lenny Kravitz, Elvis Costello, Brian Setzer, Tom Petty, the Baha Men, Jan Hooks, Adam West, Burt Ward, Larry Holmes, David Lander, Little Richard, Elliott Gould, Pamela Reed, Lisa Leslie, Tony Hawk, Blink-182, Jane Kaczmarek, James L. Brooks, Helen Fielding, Marisa Tomei, Eric Idle, Weird Al, Ben Schatz, Scott Thompson, David Byrne, Andy Serkis, Jonathan Taylor Thomas, Stacy Keach, John Kassir, Jackson Browne, Steve Buscemi, and Jane Kaczmarek.
Best Episode: “How I Spent My Strummer Vacation”
Most Emblematic Episode of the Season As a Whole: “Barting Over,” because this was The Simpsons‘ 300th episode, a milestone South Park STILL hasn’t reached and King of the Hill never did. I don’t know whether that’s a good thing or a bad thing, but, um, who’d like to be a bass player?
#14. Season 16 (2004–2005)
Every Guest Star: James Caan, Thomas Pynchon, Kim Cattrall, Eric Idle, Tom Brady, Warren Sapp, LeBron James, Yao Ming, Michelle Kwan, Gary Busey, Lucy Liu, Robert Wagner, Frank Gehry, Charles Napier, Amy Poehler, John DiMaggio, Ray Romano, Stephen Hawkins, Albert Brooks, Fantasia Barrino, Jason Bateman, and Liam Neeson.
Best Episode: “Don’t Fear the Roofer”
Most Emblematic Episode of the Season As a Whole: “There’s Something About Marrying,” because unlike “Homer’s Phobia,” which beautifully dealt with the topic of homosexuality, this episode yearned to be a HOT TAKE. The current-day Simpsons is so proud of its occasional ability to push buttons, unlike before, when it naturally happened in the writing process. Before “Marrying” aired, there was a massive publicity campaign over which long-time Simpsons character would come out of the closet. Turns out, it was Patty, but the moment didn’t feel earned; it felt like The Simpsons wanted to be the EDGY show it once was.
#13. Season 13 (2001–2002)
Every Guest Star: Pierce Brosnan, Matthew Perry, Jane Kaczmarek, R.E.M., Julia Louis-Dreyfus, George Takei, Paul Newman, Judith Owen, Richard Gere, Delroy Lindo, Ben Stiller, John Kassir, Jon Lovitz, Reese Witherspoon, Wolfgang Puck, Dennis Weaver, Frank Welker, Olympia Dukakis, Bill Saluga, Phish, Stan Lee, James Lipton, Robert Pinsky, Carmen Electra, and Frances Sternhagen.
Best Episode: “The Blunder Years”
Most Emblematic Episode of the Season As a Whole: “Jaws Wired Shut,” because that boner joke still hurts.
#12. Season 11 (1999–2000)
Every Guest Star: Mel Gibson, Jack Burns, Mark McGwire, Ed Asner, Dick Clark, Tom Arnold, Lucy Lawless, the B-52′s, Ron Howard, Pat O’Brien, Nancy O’Dell, Penn & Teller, Garry Marshall, Butch Patrick, John Goodman, Henry Winkler, Jay North, NRBQ, Gary Coleman, Tim Robbins, Clarence Clemons, Elwood Edwards, Don Cheadle, Britney Spears, Bachman–Turner Overdrive, Jim Cummings, Shawn Colvin, Betty White, Kid Rock, Joe C., Robert Evans, Charlie Rose, Diedrich Bader, Parker Posey, Jim Forbes, and Willie Nelson.
Best Episode: “Behind the Laughter”
Most Emblematic Episode of the Season As a Whole: “Kill the Alligator and Run,” because this was the year where everything began to fall apart. Honestly, I don’t hate “Alligator” as much as everyone else does, but its “wacky” story arc — Homer has a nervous breakdown, the Simpsons visit Florida, Homer kills a pet alligator — was one of many this season that would have been tossed aside by the writers only two years prior. The killer jockeys, the poison eclair, the motorcycle, Lisa as the President of the United States of the America: all horrible concepts that even the brilliant likes of John Swartzwelder and George Meyer couldn’t redeem.
#11. Season 12 (2000–2001)
Every Guest Star: The Who, Drew Barrymore, Amy Tan, Stephen King, John Updike, Jay Mohr, Joshua Jackson, Leeza Gibbons, Patrick McGoohan, Edward Norton, Michael Keaton, Charles Napier, Robert Schimmel, Bruce Vilanch, Tom Savini, Andre Agassi, Pete Sampras, Venus Williams, Serena Williams, Gary Coleman, ‘N Sync, Stacy Keach, Kathy Griffin, Frankie Muniz, and Shawn Colvin.
Best Episode: “A Tale of Two Springfields”
Most Emblematic Episode of the Season As a Whole: “Tennis the Menace,” because this episode was meant as a “screw you,” to quote writer Ian Maxtone-Graham, to viewers. The Simpsons often employs the gimmick of a first act having nothing to do with what followed, but on “Tennis the Menace,” Homer acknowledges the change by looking at the camera and taunting, “I’ll bet you didn’t see that coming!” Just ’cause it’s meta doesn’t mean it’s funny..
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