All 25 Seasons Of ‘The Simpsons,’ Ranked

The greatest sitcom, if not the greatest TV show in general, of all-time is still on, and people rarely talk about it. The Simpsons has been on for so long, has aired so many episodes, has blown through so many guest stars that it’s easy to forget, oh yeah, the program that gave us “Secrets of a Successful Marriage” is still around. I’d say it’s a shame, that a decade of occasionally great, sometimes bad, usually fine seasons has hurt The Simpsons‘ legacy, but it hasn’t: season 2-8 (or thereabout) are still as widely praised as any run a TV show has ever gone on, and even if it runs for 15 more years, at least we’ve still got “Homie the Clown” and “Marge vs. the Monorail.”

This past Sunday was the beginning of The Simpsons‘ 25th season, so because I was feeling nostalgic, and wanted a reason to talk about “You Only Move Twice,” I’ve ranked all of them, from least to most essential.

#25. Season 24 (2012–2013)

Every Guest Star: Ken Burns, Zooey Deschanel, Sarah Michelle Gellar, Anne Hathaway, Don Pardo, Natalie Portman, Al Roker, Sarah Silverman, Jon Lovitz, Jeff Gordon, Jennifer Tilly, Anika Noni Rose, Marvin Hamlisch, Steve Carell, Alex Trebek, Fred Armisen, Carrie Brownstein, Patton Oswalt, The Decemberists, Tom Waits, Valerie Harper, Danny DeVito, Rashida Jones, Benedict Cumberbatch, Robert Caro, Max Weinberg, Richard Dawkins, Tina Fey, Janet Reno, Wanda Sykes, George Takei, Edward Norton, Tony Bennett, Sonny Rollins, Ron Taylor, Justin Bieber, Bill Hader, Jane Krakowski, Patrick Stewart, Sigur Rós, Lisa Lampanelli, and Seth MacFarlane.

Best Episode: “The Day the Earth Stood Cool”
Most Emblematic Episode of the Season As a Whole: “Moonshine River,” because it brought back characters from post-golden era seasons that even hardcore fans would have trouble recalling. Remember when Anne Hathaway played Jenny in season 20’s “The Good, the Sad and the Drugly,” or Sarah Silverman as Nikki in season 21’s “Stealing First Base”? Me neither, and yet, they, along with two more former-love interests of Bart’s, returned in “Moonshine River,” a sort-of sequel to the far superior “The City of New York vs. Homer Simpson.”

#24. Season 25 (2013–2014)

Every Guest Star (So Far): Kristen Wiig

Best Episode: “Homerland”
Most Emblematic Episode of the Season As a Whole: “Homerland,” because season 24 was THAT bad.

#23. Season 20 (2008–2009)

Every Guest Star: Julia Louis-Dreyfus, Robert Forster, Denis Leary, Brian Grazer, Joe Montana, Will Shortz, Merl Reagle, Scott Thompson, Shohreh Aghdashloo, Mark Cuban, Jeff Bezos, Marv Albert, Emily Blunt, Fall Out Boy, Ed Begley, Jr., Colm Meaney, Glen Hansard, Markéta Irglová, Anne Hathaway, and Ellen Page.

Best Episode: “Lisa the Drama Queen”
Most Emblematic Episode of the Season As a Whole: “Homer and Lisa Exchange Cross Words,” because it shows Homer at his cruelest. He starts a company where he breaks up romantic relationships for their cowardly partners, AND bets against Lisa in a crossword puzzle competition. “Lisa the Greek,” it ain’t.

#22. Season 22 (2010–2011)

Every Guest Star: Jemaine Clement, Bret McKenzie, Ira Glass, Stephen Hawking, Lea Michele, Cory Monteith, Amber Riley, Mark Zuckerberg, Muhammad Yunus, Chris Hansen, Mike Scioscia, Bill James, Hugh Laurie, Daniel Radcliffe, Danica Patrick, Rachel Weisz, Martha Stewart, Katy Perry, Jon Hamm, Alyson Hannigan, Kristen Wiig, Scott Thompson, Michael Paul Chan, James Lipton, Garry Marshall, David Mamet, Ricky Gervais, Halle Berry, Russell Brand, Nick Park, J. B. Smoove, Werner Herzog, Tommy Chong, Cheech Marin, Martin Landau, Jack McBrayer, Ricky Jay, Penn & Teller, David Copperfield, Kristen Schaal, Ken Burns, and Joey Kramer.

Best Episode: “MoneyBART”
Most Emblematic Episode of the Season As a Whole: “Flaming Moe,” because I love the editorializing in the Wikipedia description for this episode: “Moe Szyslak and Waylon Smithers turn Moe’s tavern into an ultra-trendy gay bar after Smithers is rejected from Mr. Burns’s will and Moe’s business is (once again) in a slump.” “Once again.” Moe’s Tavern has gone through as many changes as Comic Book Guy has tacos in a wheelbarrow.

#21. Season 15 (2003–2004)

Every Guest Star: Jerry Lewis, Dudley Herschbach, Jennifer Garner, Oscar De La Hoya, Glenn Close, Michael Moore, Tony Blair, J.K. Rowling, Ian McKellen, Jane Leeves, Evan Marriott, Charles Napier, Jackie Mason, Mr. T, Mary-Kate and Ashley Olsen, Thomas Pynchon, Tom Clancy, Isabel Sanford, Nick Bakay, William Daniels, Dick Tufeld, Simon Cowell, Jon Lovitz, Brave Combo, Sarah Michelle Gellar, Charles Napier, and Nichelle Nichols

Best Episode: “The President Wore Pearls”
Most Emblematic Episode of the Season As a Whole: “I, (Annoyed Grunt)-Bot,” because BattleBots was popular in 2001. This episode aired in 2004. That’s late even by The Simpsons‘ always-delayed production cycle. (This was also the last season John Swartzwelder wrote an episode for.)

#20. Season 21 (2009–2010)

Every Guest Star: Seth Rogen, Chuck Liddell, Jonah Hill, Neve Campbell, Eli Manning, Peyton Manning, Cooper Manning, Kim Cattrall, Jordan Nagai, Huell Howser, the Smothers Brothers, Mitch Albom, Anne Hathaway, Gary Larson, Jackie Mason, Eartha Kitt, Chris Martin, Bob Costas, Wren T. Brown, Sarah Silverman, Angela Bassett, Sacha Baron Cohen, Yael Naim, Jane Kaczmarek, Eddie Izzard, Don Pardo, Simon Cowell, Randy Jackson, Ellen DeGeneres, Kara DioGuardi, Ryan Seacrest, and Rupert Murdoch.

Best Episode: “Thursdays with Abie”
Most Emblematic Episode of the Season As a Whole: “The Greatest Story Ever D’ohed,” because there’s no reason the Simpsons had to visit Israel. Australia, London, Brazil, Delaware, Africa, India? Sure, whatever, but whereas those episodes work to varying degrees, “The Greatest Story Ever D’ohed” wants to be subversive and make a larger point about religion and blah blah blah all faiths coming together blah blah blah, and ultimately fails. Plus, Homer’s a Carolina Panthers fan (like me!) now? Wut.

#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..

#10. Season 9 (1997–1998)

Every Guest Star: Martin Sheen, Fyvush Finkel, Joe Namath, Roy Firestone, Mike Judge, Jan Hooks, Andrea Martin, Stephen Jay Gould, Alex Trebek, Jim Varney, James Earl Jones, Jay Leno, Janeane Garofalo, Bobcat Goldthwait, Hank Williams Jr., Steven Wright, Bruce Baum, Helen Hunt, Bob Denver, Rod Steiger, Paul Winfield, U2, Steve Martin, Brendan Fraser, and Steven Weber.

Best Episode: “The City of New York vs. Homer Simpson”
Most Emblematic Episode of the Season As a Whole: “The Principal and the Pauper,” because, oh boy. Tens of thousands of all-uppercase words have been angrily written about Armin Tamzarian, which is unfair to season nine as a whole. Fans tend to think that episode speaks for the other 24 around it, but “The City of New York vs. Homer Simpson” is a classic, as are “The Cartridge Family,” “Bart Star,” and “The Joy of Sect,” among others.

#9. Season 1 (1989–1990)

Every Guest Star: Sam McMurray, Ron Taylor, Albert Brooks, June Foray, Penny Marshall, and Paul Willson.

Best Episode: “Moaning Lisa”
Most Emblematic Episode of the Season As a Whole: “Moaning Lisa,” because this was the first episode in which one of the characters, Lisa, felt fully formed and consistent with how they’d be written two decades down the line. “Simpsons Roasting on an Open Fire” is a solid, if poorly animated pilot, if you want to call it that, but “Moaning Lisa” is the first masterpiece for the eventual-greatest sitcom of all-time.

#8. Season 10 (1998–1999)

Every Guest Star: Lisa Kudrow, William Daniels, Regis Philbin, Kathie Lee Gifford, Jerry Springer, Ed McMahon, Robert Englund, Alec Baldwin, Kim Basinger, Ron Howard, Brian Grazer, George Carlin, Martin Mull, Mark Hamill, the Moody Blues, Cyndi Lauper, John Madden, Troy Aikman, Dan Marino, Pat Summerall, Rosey Grier, Fred Willard, Dolly Parton, Rupert Murdoch, Ed Begley, Jr., Elton John, Jan Hooks, John Kassir, Hank Williams, Jr., Jasper Johns, Isabella Rossellini, Jack LaLanne, Michael McKean, Stephen Hawking, George Takei, Gedde Watanabe, Keone Young, Karen Maruyama, and Denice Kumagai.

Best Episode: “Homer to the Max”
Most Emblematic Episode of the Season As a Whole: “Sunday, Cruddy Sunday,” because it’s a very good episode that should have been a disaster. It’s the first non-“Treehouse,” non-“22 Short Films About Springfield” episode that was written by more than three people. In fact, it was written by four, one of whom, Mike Scully, said it was quickly thrown together, without thinking of “things such as thought and structure.” And yet, it still turned out exceptionally because even after a decade, The Simpsons was unstoppable.

#7. Season 2 (1990–1991)

Every Guest Star: Harvey Fierstein, James Earl Jones, Tom Poston, Tony Bennett, Alex Rocco, Larry King, George Takei, Jon Lovitz, Danny DeVito, Tracey Ullman, Audrey Meadows, Ringo Starr, Dustin Hoffman, Cloris Leachman, and Daniel Stern.

Best Episode: “Lisa’s Substitute”
Most Emblematic Episode of the Season As a Whole: “Lisa’s Substitute,” because *begins crying*. In season two, The Simpsons was still very much a “normal” sitcom about a family…that just so happened to be yellow. The plots were easy to relate to, the guest stars were kept to a minimum, and Bart hadn’t won an elephant yet. Season two was more of a promising evolution from season one than a sign of what was to come.

#6. Season 3 (1991–1992)

Every Guest Star: Michael Jackson, Kipp Lennon, Neil Patrick Harris, Magic Johnson, Chick Hearn, Jon Lovitz, Jackie Mason, Frank Welker, Aerosmith, Sting, Wade Boggs, Jose Canseco, Roger Clemens, Ken Griffey, Jr., Don Mattingly, Steve Sax, Mike Scioscia, Ozzie Smith, Terry Cashman, Darryl Strawberry, Steve Allen, Beverly D’Angelo, Christopher Guest, Michael McKean, Kimmy Robertson, Danny DeVito, and Joe Frazier.

Best Episode: “Homer at the Bat”
Most Emblematic Episode of the Season As a Whole: “Stark Raving Dad,” because it’s the premiere, and season three is the beginning of The Simpsons multi-season run of perfection. Yes, “Stark Raving Dad” was a holdover from season two, but it FEELS like a season three episode, with a major guest star (“John Jay Smith”) seamlessly blending into Springfield’s ever-expanding universe. It’s heartfelt, but not saccharine and always funny, which goes for the entirety of the season, too.

#5. Season 8 (1996–1997)

Every Guest Star: Albert Brooks, Michael Buffer, Paul Winfield, Rodney Dangerfield, Johnny Cash, Leonard Nimoy, David Duchovny, Gillian Anderson, Jack Lemmon, Joe Mantegna, Alex Rocco, Jon Waters, David Hyde Pierce, Dave Thomas, Bret Hart, Denise Kumagal, Karen Maruyama, Sab Shimono, Gedde Watanabe, Tim Conway, Gailard Sartain, and William Dafoe.

Best Episode: “You Only Move Twice”
Most Emblematic Episode of the Season As a Whole: “The Itchy & Scratchy & Poochie Show,” because in this episode, as well as “The Springfield Files,” “You Only Move Twice,” “El Viaje Misterioso de Nuestro Jomer (The Mysterious Voyage of Homer),” and “The Simpsons Spin-Off Showcase,” The Simpsons was taking weirder and weirder conceptual chances, and they all worked. Even the highly controversial “Homer’s Enemy,” a turning point of the series for many, got away with turning Homer into an asshole, because the script was tight enough to allow him to be. (As a personal aside, season eight’s animation is my favorite of the entire show.)

#4. Season 7 (1995–1996)

Every Guest Star: Tito Puente, Mickey Rooney, Joan Kenley, Paul McCartney, Linda McCartney, Paul Anka, Glenn Close, Harry Morgan, R. Lee Ermey, Lawrence Tierney, Tom Kite, Bob Newhart, Donald Sutherland, Suzanne Somers, Kirk Douglas, Alex Rocco, Jack Sheldon, Jeff Goldblum, the Smashing Pumpkins, Cypress Hill, Sonic Youth, Peter Frampton, and Christina Ricci.

Best Episode: “Summer of 4 Ft. 2”
Most Emblematic Episode of the Season As a Whole: “The Simpsons 138th Episode Spectacular,” because this is the season where Bill Oakley and Josh Weinstein took over as showrunners, and they wanted The Simpsons to go back to feeling more realistic, with an occasional outlier. And that’s how you go from “I’m Troy McClure, and I’ll leave you with what we all came here to see: hardcore nudity!” to “Milhouse, do you ever worry that your mom might stop loving you?”

#3. Season 6 (1994–1995)

Every Guest Star: Winona Ryder, Larry King, Dr. Demento, James Earl Jones, Meryl Streep, Dennis Franz, Anne Bancroft, Ted Danson, Woody Harrelson, Rhea Perlman, John Ratzenberger, George Wendt, Patrick Stewart, Dick Cavett, Johnny Unitas, Susan Sarandon, Mel Brooks, Mandy Patinkin, Ron Taylor, Steve Allen, and Tito Puente.

Best Episode: “Homer Badman”
Most Emblematic Episode of the Season As a Whole: “Who Shot Mr. Burns? (Part One),” because I’m running out of ways to say how great The Simpsons is and this feels like An Episode That Matters. (Another episode that fits the criteria: “A Star Is Burns,” which Matt Groening infamously took his name off of because he felt it was blatant advertisement for Fox’s The Critic, created by two former Simpsons writer, Mike Reiss and Al Jean. Thing is, it’s great, and the reason they were asked to help out was because Fox demanded 25 episodes, a number the then-current Simpsons writers felt was too much, so Reiss and Jean pitched in with “Burns” and “‘Round Springfield.” That, my friends, is the rare good kind of network interference.)

#2. Season 5 (1993–1994)

Every Guest Star: George Harrison, David Crosby, the Ramones, Frank Welker, George Fenneman, Pamela Reed, James Brown, Albert Brooks, Ernest Borgnine, Michelle Pfeiffer, Werner Klemperer, Robert Goulet, Gerry Cooney, Sam Neill, Conan O’Brien, James Woods, Kathleen Turner, Buzz Aldrin, and James Taylor.

Best Episode: “Homer Goes to College”
Most Emblematic Episode of the Season As a Whole: “Homer and Apu,” because 1) The Simpsons was experimenting with unusual pairings and turning previously undeveloped Springfield citizens into fan favorite main characters, and 2) You can’t beat going from “Homer’s Barbershop Quartet” to “Cape Feare” to “Homer Goes to College” to “Rosebud.” Wait. Actually, you can…

#1. Season 4 (1992–1993)

Every Guest Star: Bob Hope, Tom Jones, Sara Gilbert, Pamela Reed, Linda Ronstadt, Adam West, Elizabeth Taylor, Leonard Nimoy, Dr. Joyce Brothers, Brooke Shields, David Crosby, Johnny Carson, Hugh Hefner, Bette Midler, Barry White, Luke Perry, Elizabeth Taylor, and Red Hot Chili Peppers.

Best Episode: “Last Exit to Springfield”
Most Emblematic Episode of the Season As a Whole: “Last Exit to Springfield,” because every line is perfect, just as every episode from season four is perfect. TV at its best.