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There was no way in hell MILF Island was getting on the air. Not if NBC’s broadcast standards and practices department had its way.

In the Season 2 of 30 Rock, television executive Jack Donaghy (Alec Baldwin) scores a huge hit with an outrageously inappropriate reality show based on an outrageously inappropriate premise: “20 MILFs, 50 eighth-grade boys. No rules.”

In real life, the censor objected to the naughty acronym, which you couldn’t fully explain on the air without a bleep. “Standards didn’t want us to say the word ‘MILF’ at all,” recalls 30 Rock showrunner Robert Carlock. “It was like, ‘Yeah, you’re right, but we’re going to push and try to do it.’” 

Eventually, the network caved. “And it was really funny and not something you want to explain to your kids when they are old enough to watch 30 Rock,” Carlock says. “It’s ridiculous. It’s stupid.”

And also surreally prescient. In late 2022, TLC announced a new reality show called MILF Manor. The premise will sound eerily familiar: “Eight hot moms leave home for the chance to find love with men half their age, but they’re greeted with a shocking twist.” The series ran for two seasons.

This kind of thing isn’t terribly shocking to Tina Fey, the creator and star of 30 Rock. In that world, fictional entertainment often barely felt like fiction. “Most of the fake shows were just heightened versions of what was already happening,” Fey says over email. “So yeah, not surprised that we actually ended up with MILF Island. We’re a fallen society.”

When 30 Rock premiered on October 11, 2006, it was unique: a workplace comedy about the making of a late-night sketch show. It found laughs in an unlikely male-female friendship, the joys of eating cheese, and most of all, the derangement of creative people buckling under the weight of ego and anxiety. 

Despite what you may have heard about the glory days of Saturday Night Live, a chaotic and pressure-packed environment doesn’t always produce great art. Sometimes it just leads to bad TV. That’s what 30 Rock celebrated. For seven seasons, it gave us fake sketches, shows, movies, and songs that were hilarious in their awfulness.

Some are stupid-funny (“Fart Doctor”). Some are just a little too close to actual programming on ESPN (Sports Shouting). Some are reality shows that you’d actually want to see on Bravo (Queen of Jordan). Some are razor-sharp satires of the self-help industry (Dealbreakers). And some rag on the shamelessness of showbiz (America’s Kidz Got Singing). But all of them are fully realized.

Since its debut, no sitcom has committed to the bit as intently—or intensely—as 30 Rock. There was never a parody too big or small to turn into an elaborately filmed digression. That’s why Jack McBrayer, who played page Kenneth Parcell, calls the show “a live-action cartoon.”

Hardcore fans of the series have spent the last 20 years collecting its hyper-meta cutaway jokes. For them, there’s no gag that’s too esoteric to reference … or turn into a Halloween costume.

“Mean Girls gets quoted back to me a lot—brag much?—but the 30 Rock people,” Fey says, “they are the Elvis Costello fans of comedy.”


Working at Saturday Night Live taught Carlock two important lessons:

1. “Writing good sketches, that’s really, really hard to do.”
2. “Tina was a lot better at it than I was. She’s probably one of the best ever.”

Fey was the head writer at SNL for seven years, co-hosted “Weekend Update,” and appeared in dozens of sketches. In other words, she was the perfect person to play someone in charge of 30 Rock’s  show-within-the-show. But it was decided early on in development that Liz Lemon (Fey) would not be presiding over an American institution. The Girlie Show with Tracy Jordan would be an absolute mess.

Embracing that idea was freeing. After all, it’s a live sketch show. There are always going to be some duds. Plus, you can’t look away from a trainwreck. “It was something that very quickly became really fun,” Carlock says. “Why wouldn’t we want to see that?”

At first, that meant coming up with bad TGS sketches. Then the 30 Rock writers started thinking bigger. “Now we’re living in a world where we’re creating a fictional NBC,” Carlock says. A fictional NBC needed fake shows. And fake shows snowballed into fake … everything. Cheesy Blasters anyone? 

Like the vast majority of Gen X comedy writers, Carlock was a big Simpsons fan. The creators of the animated series packed its episodes with cutaway jokes. 30 Rock brought that approach into the real (fake) world. “We had what is maybe more of an animated sensibility than a live-action single-cam sensibility,” Carlock says.

Seeing Tracy Jordan (Tracy Morgan), say, playing every family member in The Chunks 2: A Very Chunky Christmas was funnier than just hearing him talk about it. “The logic was that the cutaways replaced what the characters would have been describing in that moment,” Fey says.

Not surprised that we actually ended up with MILF Island. We’re a fallen society
Tina Fey

At the beginning, the writers started small. “One of the first things that we were cutting away to was ‘Robot/Bear Talk Show,’” Carlock says. (The TGS sketch is exactly what it sounds like.) Their pitches gradually became more ambitious. Though some of their most conceptual ideas came from their most mundane conversations.

The first season of 30 Rock came together in a writers room in Hell’s Kitchen. One day, Fey remembers laughing about how she could never correctly pronounce the word “rural.” That discussion led to a movie called The Rural Juror, based on a book by Kevin Grisham … John Grisham’s brother. Jenna Maroney (Jane Krakowski) plays the lead: Constance Justice. No one at TGS can decipher the title of the fake legal thriller because Jenna can’t say it clearly. “So many jokes and stories came out of just talking before beginning our actual work,” Fey says. “Room bits.”

Early Simpsons writers often talk about how time-consuming—and mentally exhausting—it was to regularly think up good cutaway jokes. But to Fey, they were a reward for figuring out the rest of an episode. “They were a treat to write,” she says. “The harder thing to do is break stories that make emotional sense. That’s the worst!”


For McBrayer, flipping through a 30 Rock script “was like opening a Christmas present.” Every episode brought new surprises for Kenneth the page. “I mean, I knew what outfit I was going to be wearing,” he says. But nothing else.

One week Kenneth’s inspiring Jack to green-light a game show called Gold Case. It doesn’t last because the contestants can always easily guess which model is holding the briefcase filled with $1 million in solid gold—by her wobbly arms and the pained look on her face.

The next week Kenneth’s sharing an office with the writers of the fake Boston sports show Bruins Beat: “They’re all named Sean, they are mean, and I hate it here.”

McBrayer noticed pretty early into 30 Rock’s run that the writers were really leaning into bits like that. “The cutaways started becoming a little more frequent and hilarious and non sequitur-y,” he says. “And it was really a joy to see how much fun the writers were having with those kinds of ideas.”

That was no accident. Early on, there was a good reason why Carlock and Fey decided to throw the comedic kitchen sink at every episode: they were afraid NBC was going to cancel the show. Their mantra became, Carlock says, “Let’s do it because I don’t know if this is going to last.”

But then NBC picked up 30 Rock for a second season. And then five more. “Once it felt like it was going to last for as long as it did, which was wonderful, we were stuck with it in a certain way,” Carlock says. “And I think we love that rhythm.”

It’s hard for him to pick a single favorite 30 Rock cutaway, but one Carlock loves is Homonym!. On the game show, a contestant is given a word with two meanings and has to choose the correct definition. “The bit is they never have to pay the money out,” Carlock says. The host, Steve Higgins, responds to every answer by saying, “Sorry, it’s the other one.”

Fey’s partial to Tennis Night in America, Jack’s attempt to turn a country club sport into the NFL. Jenna even sings the show’s country theme song, which goes something like this: “Got some buds and some brews, it’s gonna be a fight / So put down your meth, slip on your whites / ’cause here in real America it’s tennis night.” As Fey puts it: “It captures the stupid red state vs. blue state nonsense in our culture.”

A parody like that is only possible when you have a cast that’s unafraid to look deeply silly. “We like to find actors who are really funny and willing to say yes to anything,” Carlock says. That’s why Krakowski and Morgan work so well as Jenna and Tracy.

“There’s the old joke of, ‘Oh, he’d be funny reading the phone book,’” Carlock says. “We literally did have Tracy eventually on 30 Rock do a story where he was trying to get his EGOT and there was a scene where his one-man show to try to get a Tony was him reading the phone book. And we just had him read the phone book. Him saying, ‘Aaronson, Alan,’ is funny. And hopefully it doesn’t make you lazy as a writer just because you have that. What’s funny about it is he has a funny voice. And it is the dead-eyed commitment.”

To her credit, Krakowski threw herself into every single one of Jenna’s misguided fake projects. “Working with Jane was such a joy because she was so committed, so prepared, and also she’s a pro after all those years on Broadway. She’s just so physical with her acting,” McBrayer says. “...Jane Krakowski was not afraid to look weird.”

Like, for example, in Sing Dem Blues, White Girl: The Jackie Jormp-Jomp Story. That’s Jenna’s unlicensed biopic of Janis Joplin. (Some modern music biopics have started to resemble Jackie Jormp-Jomp. In 2021, there was an unauthorized Celine Dion movie called Aline.)

At one point, Jenna’s character sings a passionate rendition of one of Joplin’s biggest hits: “Piece of My Heart.” Oops, I mean “Chunk of My Lung.”


That kind of fun was alluring. Hollywood A-listers soon wanted in on it. “You start to develop that reputation of, ‘Oh, people get to come and score.’ They get to be funny and they get to play opposite these great people,” Carlock says. “Then Matt Damon says to Tina’s development guy at a party, ‘I want to be on the show.’ And we say, ‘Be careful what you wish for.’”

Damon, who plays Liz’s pilot boyfriend, was far from the only movie star to end up on 30 Rock. When the show needed leads for Martin Luther King Day—a fake ensemble rom-com in the style of Valentine’s Day and New Year’s Eve—Fey knew who to ask. “God bless Emma Stone and Andy Samberg for saying yes,” she says.

By the end of 30 Rock, things had, well, escalated. The fake movies began to feel as fleshed out as the real movies they were parodying. Writer Luke Del Tredici’s “Leap Day,” a Season 6 episode about the quadrennial calendar quirk’s mascot Leap Day William, features a mini-film called Leap Dave Williams. “Luke Del Tredici is a great writer,” Fey says. “Leap Dave Williams was maybe the apotheosis of insanity.”

The holiday comedy stars the real Jim Carrey as Dave, an average man who transforms into the gilled and mustachioed Leap Day William. Andie MacDowell, who was in Groundhog Day, plays his love interest.

“It was like, ‘We want to make fun of a Jim Carrey movie, what if we try to get Jim Carrey?’” Carlock says. Naturally, Carrey said yes.

“The scene of him running down the sidewalk tearing his clothes off,” Carlock says. “That was just supposed to be him running down the sidewalk. I think he always brings his A-game. You would have people like that show up ready to play in our stupid sandbox.”


These days, having a sandbox like that to play in is increasingly rare. Television production budgets are way down. Fewer and fewer sitcoms are cultural touchstones. In other words, 30 Rock is a relic. But for a while, NBC—which is still making comedies for broadcast TV and streaming—let the show run wild.

For that, Carlock is eternally thankful. “When you’re an investment, when there’s payoff to the back end, they’ll invest in you,” he says. “It doesn’t happen so much anymore. But we had a stint.” Running a live-action cartoon for almost a decade, he adds, led to a lot of conversations like this: 

“Are we really building the set?” 
“Yeah. We’re going to build the set.”

Hey, the living room in Black Frasier had to look exactly like the one in Frasier. Otherwise it wouldn’t be a serious joke. Until the very end, there was no gag 30 Rock didn’t fully commit to.

“In the final episode there was a sketch, and Jane and Tracy both had this really emotional, ‘I’m going to miss you,’ moment while they’re both dressed like Hitler in full Hitler drag,” Carlock says. “It was a different time.”

Leap Dave Williams was maybe the apotheosis of insanity
Tina Fey

And now, exactly 20 years after the premiere, the cast of 30 Rock is reuniting—for one night only. On October 11, Fey, Krakowski, Morgan, McBrayer, and Baldwin will be at Radio City Music Hall for an anniversary celebration. “I don’t even know what the show is,” McBrayer says, “but we’re going to have a blast.”

It’s a safe bet that there’ll be some fake movies and shows. And maybe a fake song or two. To this day, Carlock remembers coming up with the most memorable piece of fake pop music in the history of 30 Rock: “Werewolf Bar Mitzvah.” Tracy Jordan’s novelty hit from Season 2 was the showrunner’s idea, but making it was a collaborative effort.

Writer Tami Sagher suggested the chorus: “Boys becoming men / men becoming wolves…” Composer Jeff Richmond wrote the music, first starting with a short snippet. Fey suggested doing a full version and putting it on YouTube. Morgan recorded the vocals. And Donald Glover, who was writing for the show at the time, came in as a skeptical hypeman. Then they had a real track—that’s now a goofy Halloween staple.

Carlock didn’t think too much about the song’s legacy until a few years ago, when his older daughter started hearing it at her friends’ bat mitzvah parties. “It was 20 years later,” he says. “But that’s when it sunk in.”

In true 30 Rock fashion, they found joy in bad art.

Alan Siegel
Alan Siegel
Alan covers a mix of movies, music, TV, and general nostalgia. He lives in Los Angeles and is the author of ‘Stupid TV, Be More Funny: How the Golden Era of “The Simpsons” Changed Television—and America—Forever.’

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