I've watched all 139 episodes of "30 Rock" plus the pandemic special, and it's time to pick some favorites. Narrowing this list down to ten entries was tough, so the honorable mentions list is pretty hefty.
Episodes are unranked and listed by airdate. Spoilers ahead.
"Black Tie" - One of the first big format breaking episodes, and the first to feature some major guest stars: Paul Reubens and Isabella Rossellini. The two of them are given so much fun material, it's no wonder that "30 Rock" was able to convince so many other big celebrities to drop by over the years. This is also the closest that Jack and Liz ever got to a romance, subverted of course in the end, but it's nice to think about the possibilities.
"Rosemary's Baby" - Even if the rest of the episode doesn't match up to it, I can't in good conscience leave off the episode with Jack Donaghy's award-winning trip to the therapist to help Tracy with some of his unresolved parental issues. Alec Baldwin channeling "Good Times," "To Kill a Mockingbird," and Mrs. Rodriguez is one of the comedy highlights of 21st century television, and even though I didn't watch "30 Rock" in 2007, I knew that clip.
"Reunion" - "30 Rock" was always very good about subverting typical sitcom plots, and Liz Lemon's high school reunion was a doozy. The show has established that Liz is terrible, and now we find out that she was always terrible. Even if she was the stereotypical nerd, she was also the mean girl, and is forced to confront her own villainy. To cap it all off, we have a "Carrie" homage gone wrong and Jack getting in on the fun as Larry Braverman.
"Generalissimo" - If it wasn't obvious by now, Jack Donaghy is my favorite character. "Generalissimo" gives us the first of his many doubles, in this case an actor on a Mexican telenovela who plays the evil Generalissimo, a character hated by his girlfriend's grandmother. Cue Baldwin in a mustache. This was also the first episode for Jon Hamm as Drew, who proceeded to get more and more dimwitted with every subsequent appearance.
"Klaus and Greta" - The one with James Franco and a body pillow. This is a strong ensemble episode, with Jack and Kenneth breaking into Nancy's house to erase a phone message, Jenna in a fake relationship with James Franco (playing himself), Liz trying to help her gay cousin, and Tracy overcorrecting his attitudes toward women to prepare for becoming a girl dad. The show was on a hot streak in season four, and this was one of the highs.
"Anna Howard Shaw Day" - "30 Rock" did Valentine's Day episodes better than most other sitcoms, because it understands that Valentine's Day is always awful. This is where Jack first meets Avery, who is easily the best of his romantic interests, and Liz has to find a ride home after her root canal. The way the two subplots converge is perfect, and I love that all of Liz's exes stick around for a final gag, playing her hallucinations of the Afro-Caribbean nurses.
"Double Edged Sword" - Jack and Avery are stuck in Canada while Liz and Carroll are stuck on the tarmac, forcing both couples to evaluate their relationships. Jack and Avery are a fantastic comedic pair, and I always love them being elitist snobs together, especially in a crisis where John Cho has to sneak them over the border. Meanwhile, the end of Carroll's arc was inevitable, but what a way to go out! The absurd airplane standoff is one of the best moments in the show.
"Live From Studio 6H" - Yes, the live show where Jon Hamm briefly shows up in blackface, which leads to some great commentary on how racist TV used to be (and still is), and enables some righteous and very funny rage from Tracy. Kenneth presenting a history of live television means all kinds of costume changes and everybody playing multiple roles. Amy Poehler and Donald Glover also shine in guest parts - plus a Beatle or a Kardashian depending on which version of the episode you're watching.
"Mazel Tov, Dummies!" - Liz finally gets married, after spending most of the episode trying very hard not to make a big deal out of her wedding. I've never felt closer to a fictional character as I have with Liz Lemon here, valiantly trying not to follow social expectations, and deciding in the end that it's okay to want something. The wedding itself was exactly what it should have been, and I'm glad the writers resisted getting the whole "TGS" crew involved to complicate matters.
"A Goon's Deed in a Weary World" - The more I think about it, the more I'm sure that this should have been the last episode of "30 Rock." Liz is finally convinced to let the show go, with help from her whole writing staff. And after an extended "Willy Wonka" spoof, Jack anoints his successor, and Kenneth finally gets a capper to his multi-season search for a better job. I understand the actual finale has to subvert all the usual tropes of sitcom finales, but I'm a sucker for a happy ending.
Honorable Mentions: "Tracy Does Conan," "Up All Night," "SeinfeldVision," "Subway Hero," "Sandwich Day," "Believe in the Stars," "Gavin Volure," "Floyd," "The Moms," "Emmanuelle Goes to Dinosaur Land," "Reaganing," "TGS Hates Women," "Queen of Jordan," "100," "Leap Day," and "My Whole Life is Thunder."
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