#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.
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