If you know 30 Rock, you know one of its main comedic selling points was guest stars.
The show didn’tneedthem — its main characters are funny enough. But since 30 Rock is a comedy about the entertainment industry, it makes sense that celebrities would always show up as themselves or fictional characters.
However, which of these dozens upon dozens of guest appearances stand out as the best? (In the interest of brevity, I’m excluding long-term recurring characters. Sorry, fans of Dr. Spaceman, Dennis Duffy, Devon Banks, or Liz and Jack’s various seasonal lovers — know that I’m one of you in spirit.)
Here are the 15 very best 30 Rock guest stars — ranked:
15. John McEnroe as Himself (Season 1 Episode 11)
On 30 Rock Season 1 Episode 11, “The Head and the Hair,” NBC Page Kenneth Parcell (Jack McBrayer) pitches the game show Gold Case.
In the style ofDeal or No DealandWho Wants to Be a Millionaire?, 1tenmodels hold up briefcases and contestants have to guess which one holds $1 million in gold bars.
The pilot is hosted by tennis star John McEnroe, who discovers firsthand the problem with the premise: Gold is heavy, so it’s easy to tell which briefcase has it. McEnroe’s demeanor goes from polite and enthusiastic game show host to irritated as each contestant keeps “striking gold.”
McEnroe makes a couple more cameos, but his first is the most memorable.
“Gold Case” was the first sign of how clever the show’s mockery of its own industry would be. Its fake-but-plausible-enough-to-be-real TV show jokes are always winners (MILF Island, anyone?).
14. Don Cheadle as Himself (Season 7 Episode 4)
During 30 Rock’s final season, the 2012 presidential election was in full swing, and the early episodes leaned into the political humor.
On 30 Rock Season 7 Episode 4, “Unwindulax,” Jack (Alec Baldwin) tries to whip up African-American support for Mitt Romney by finding a Black celebrity to endorse him. The best he can manage is paying Don Cheadle $10 million to shoot an ad “endorsing” Romney.
Cheadle struggles to recite his lines, mainly that “Mitt Romney is a layup” (he gives up trying to say it on the first take).
Since Jack couldn’t get another celeb of Cheadle’s caliber, his co-star in the ad is “The black Transformer, Jazz” (i.e. a car with a stereotypical voice). Grizz (Grizz Chapman) and Dot Com (Kevin Brown) are unimpressed by Jack’s star-studded “community organizing.”
While the specific context of the jokes may be dated, the context of Cheadle’s cameo (and the absurdity of Jazz’s) is still funny.
13. William Baldwin as Lance Drake Mandrell (Season 6 Episode 12)
Jack Donaghy doesn’t keep in touch with his siblings, but Alec Baldwin is famously part of an acting dynasty with his three brothers. 30 RockSeason 6 Episode 12, “Kidnapped By Danger,” finally capitalized on this.
William Baldwin appears as actor Lance Drake Mandrell, who is cast as Jack in the TV movie Kidnapped By Danger. The movie documents Jack’s love story with Avery Jessup (Elizabeth Banks).
Mandrell takes the method approach and gets quite into character, which is just Baldwin putting on a top-tier impression of his older brother.
Mandrell’s uncanny resemblance to Jack and perfect adoption of his mannerisms is also used to “solve” Jack’s sexual tension with his mother, Diana (Mary Steenburgen). Jack Donaghy uses a Baldwin brother to prove how 30 Rock can make obvious and self-referential humor sing.
12. John Slattery as Steve Austin (Season 5 Episode 7)
30 Rock Season 5 Episode 7, “Brooklyn Without Limits,” is about betraying your principles.
For Liz (Tina Fey), that means buying form-flattering jeans from a store that uses child labor. Jack’s actions are more disastrous.
Congresswoman Regina Bookman (Queen Latifah) is investigating NBC, so Jack sponsors her re-election opponent. The only problem is that the opponent is Steve Austin (John Slattery), who is too crazy and stupid for the Tea Party reactionary.
Austin is far from Slattery’s most famous part as blue-blooded New Yorker Roger Sterling from Mad Men (Roger, Jack would probably get along swimmingly with), but that only underlines his hilarious and dignity-free performance.
Many 30 Rock cameos are actors playing themselves, but Slattery is one of the show’s best cast-against-type cameos.
11. Steve Martin as Gavin Volure (Season 3 Episode 4)
Liz Lemon’s pursuit of the right guy leads to many of her life’s most memorable guest stars.
One of the best (for the audience at least) was Steve Martin’s portrayal of Gavin Volure on the eponymous 30 Rock Season 3 Episode 4, “Gavin Volure.”
Jack introduces Liz to Gavin, initially portrayed as an eccentric business mogul who abruptly became a shut-in years prior; he invites Jack to invest in his latest venture. Martin is, of course, one of the top comedy stars of his generation, and the charisma that got him there means we’re inclined to trust Gavin.
Then, halfway through, the episode swings into hilarity. Gavin isn’t a shut-in; he’s under house arrest for tax evasion and wants Liz to escape.
Liz Lemon’s disaster zone love life is always a treat for us, especially during “Gavin Volure.”
10. Oprah Winfrey as Herself (Season 3 Episode 2)
30 Rock Season 3 Episode 2, “Believe In The Stars,” is one of the four episodes pulled from streaming due to a scene of a white character appearing in blackface (once is an extremely careless mistake, but four times???!).
While that one flaw can’t be overlooked, the episode does have other moments more deserving of praise.
One of them is Oprah Winfrey’s cameo. On a flight back to New York, a starstruck (and sedated) Liz sits next to Mrs. Winfrey. If 30 Rock was going to be a TV satire worth its oats, then an appearance by one of the medium’s top gurus was inevitable.
As Liz lets her problems spill out, Oprah offers counsel and helps her police Tracy (Tracy Morgan) and Jenna (Jane Krakowski).
When that time comes, the bombshell drops: Liz didn’t meet Oprah, she just hallucinated that the girl sitting next to her was Oprah thanks to the sedative she took. When Liz Lemon’s subconscious needs a calming force, it summons Oprah Winfrey.
9. Jon Bon Jovi as Himself (Season 4 Episode 13)
30 Rock Season 4 Episode 13, “Anna Howard Shaw Day,” is the series’ Valentine’s Day special, but it’s named as such because Liz thinks the holiday “gives love a bad name.”
After all, when she tries a relationship, she usually winds up “shot through the heart” (ok, I’m done, I swear).
To that end, Liz books a dental surgery appointment on Valentine’s Day to prove it’s just like any other day. This backfires because no one is available to escort her home while she recovers from the anesthesia.
About two-thirds through the episode, Liz meets Jon Bon Jovi at a party thrown by Jack. He convinces her not to sign a liability waiver (i.e., put in writing that she has no one on Valentine’s Day). Bon Jovi’s appearance is a red herring.
Will he show up to rescue Liz from the dentist? Nope! Instead, Jack has to help Liz as usual. However, Liz does hallucinate that an office palm tree is Bon Jovi, showing up like her knight in shining armor.
8. Steve Buscemi as Len Wozniak (Season 2 Episode 3)
Steve Buscemi has a small role as Jack Donaghy’s go-to private investigator, Len Wozniak.
Len appears in six episodes total; first on 30 Rock Season 2 Episode 3, “The Collection,” and finally on Season 7 Episode 9, “Game Over.” (Buscemi also directed two episodes of the comedy series).
I may be cheating by including a recurring character, but Len’s roles are so minor that I’ll allow it.
His competence goes downhill across the series. In his first appearance, he’s a consummate professional. In his fifth (30 Rock Season 6 Episode 8, “The Tuxedo Begins,”), he recounts goingundercover at a high school.
This story resulted in the famous “How do you do, fellow kids?” meme. Buscemi, the great character actor that he is, passes as both a serious PI character and a parody of one.
Len’s final appearance features him going undercover as a (female) high school drama teacher. By the episode’s end, Len has decided to turn the cover into a lifestyle and live as a woman. In the words of Lucille Bluth (Jessica Walter) from Arrested Development, good for her!
7. Kelsey Grammer as Himself (Season 5 Episode 5)
Kelsey Grammer plays himself in 30 Rock,but his portrayal is characterized like another of the show’s eccentric characters.
The Frasier star is depicted as a criminal mastermind who twice helps out Jenna and Kenneth with schemes, dubbing the trio “The Best Friends Gang.” Sideshow Bob from The Simpsons has nothing on Kelsey Grammer in this show.
On 30 RockSeason 5 Episode 5, “Reaganing,” Grammer joins in on Jenna and Kenneth’s con to scam Carvel (Jenna has a lifetime free ice cream after appearing in a Carvel commercial, so the three order several cakes and then demands “refunds.”)
Then, on 30 Rock Season 6 Episode 3, “Idiots Are People Three,” Jenna and Kenneth call on Grammer’s help to avoid trouble when they accidentally expose Pete Hornberger (Scott Adsit) to a gas leak. (He’s reintroduced with a James Bond-stylesong.)
The whole scene is like a parody of fixer Winston the Wolf from Pulp Fiction. Like Keitel, Grammer, too, has the mix of commanding presence and suaveness to pull it off.
6. Peter Dinklage as Stewart LaGrange (Season 3 Episode 7)
On 30 Rock Season 3 Episode 7, “Señor Macho Solo,” Liz feels baby crazy, walks up to a “boy” and ruffles his hair.
Too bad this is actually Stewart LeGrange (Peter Dinklage), an adult man with dwarfism. To save herself embarrassment, Liz pretended she wanted to ask him out.
They hit it off — their chemistry is believable because Dinklage’s sardonic wit is a comedic match for Fey’s. Dinklage’s screen presence carries gravitas (which he’d later use to great effect as Tyrion on Game of Thrones) that makes him feel more put-together than Liz’s other love interests.
Stu works at the UN, a far cry from “Beeper Man” Dennis Duffy (Dean Winters).
Once Stu finds out the real reason they met, though, the relationship is doomed. The whole situation is a great exploration of how Liz Lemon is not a good person (and nowhere near as enlightened as she acts), but endearingsly so.
5. Matthew Broderick as Cooter Burger (Season 2 Episode 15)
At the tail end of Season 2, Jack becomes frustrated with GE (specifically him being turned down for the CEO position) and goes into the public sector.
Using his Bush contacts, he is named “Homeland Security Director for Crisis and Weather Management.” Still, he leads a pitifully underfunded bureaucracy full of beaten-down sad sacks like Cooter Burger (Matthew Broderick). His nickname (given by the then-President) is the episode’s title: 30 Rock Season 2 Episode 15, “Cooter.”
Seeing Ferris Bueller as a milquetoast public servant is some ironic casting. However, Broderick still has a strong comedic spark to make Cooter’s patheticness funny, not soul-sucking like his work is.
The coup de grace comes when Jack and Cooter spearhead the development of a “Gay bomb” to get fired and re-enter the private sector. Cooter, amazed by the Pentagon’s ready supply of pens, accidentally knocks over the chemical weapon vial.
While Cooter did not become a recurring character, Broderick returns on 30 Rock Season 7 Episode 2, “Governor Dunston,” where Cooter has become a lobbyist. This return is a testament to how memorable his original appearance was.
4. Chloë Grace Moretz as Kaylie Hooper (Season 5 Episode 16)
30 Rock Season 5 Episode 16, “TGS Hates Women,” features Cristin Milioti as Abby Flynn, a new TGS writer who acts sexualized and immature.
Liz “exposes” this as a facade, thinking Abby is trying to get ahead with sex appeal, then discovers she was actually in hiding from her abusive ex-husband. Oops! It’s a classic Liz Lemon foul-up.
However, the even more memorable guest star is Chloë Grace Moretz as Kaylie Hooper, the 15-year-old heir apparent to NBC’s parent company, KableTown.
She becomes Jack’s nemesis, and they both vie to seize the company. Moretz is perfect as both the faux-innocent teenage girl and a conniving mastermind. The absurdity of Jack squaring off with a teenage girl also keeps the corporate politicking of the storyline the appropriate comic grounding.
Kaylie’s best episode is her third and final one, 30 Rock Season 7 Episode 9, “Game Over.” Jack teams up with old nemesis Devon Banks (Will Arnett) to take down Kaylie, resulting in schemes within schemes. The episode’s climax, where Kaylie and Jack play their aces up their sleeves, is jaw-dropping and unforgettable.
3. David Schwimmer as Greenzo (Season 2 Episode 5)
30 Rock Season 2 Episode 5, “Greenzo,” was born of NBC’s 2007 environmental initiatives, including demands for its programming to convey such messages.
The sitcom, aware of how absurd it is for big businesses to fight against the pollution they cause, featured Jack attempting to create an environmentally and business-friendly company mascot.
The result is Greenzo (David Schwimmer), played by struggling actor Jared. “Greenzo” gets too into character, rabidly promoting genuine environmentalism instead of the watered-down variety Jack wanted. After Jared is fired, he still keeps the Greenzo costume and tries to play the part.
Schwimmer isn’t an unknown, but his appearance as an actor struggling for relevance and to be taken seriously (with limited success) reflects how he’s tried to change his public perception after Friends. “Greenzo” lets him be in on the joke.
2. Alan Alda as Milton Greene (Season 3 Episode 21)
After Jack discovers the man he thought was his father isn’t, 30 RockSeason 3 Episode 21, “Mamma Mia,” sees him finally meet his birth father: Milton Greene (Alan Alda).
This plot twist required a big name, and M*A*S*H star/TV comedy legend Alda was a perfectfit.
Milton is the opposite of Jack, a lefty history professor who, when they meet, is writing a biography of Jimmy Carter. Despite their differences, they hit it off.
Alda and Baldwin prove perfect scene partners both when Jack and Milton play catch or when their political differences explode.
When Milton needs a kidney transplant, Jack turns a TGS episode into a drive with musician guest stars (from Sheryl Crow to Elvis Costello).
Milton does not become a recurring part of Jack’s life (Alda, for all his chemistry with Baldwin, would probably eat up too much of the guest star budget). Still, he does return on 30 RockSeason 5 Episode 10, “Christmas Attack Zone,” where Jack finally confronts his mother, Colleen (Elaine Stritch), for lying to him about his parentage.
1. Carrie Fisher as Rosemary Howard (Season 2 Episode 4)
Liz Lemon is a big Star Wars fan. Her go-to move to get out of jury duty is to cosplay Princess Leia and pretend to be a “weirdo” who is too incompetent to stand.
Of course, the late Carrie Fisher — Leia herself — would have to appear on the show. And she did, on 30 RockSeason 2 Episode 4, “Rosemary’s Baby,” receiving an Emmy nomination.
Fisher plays Rosemary O’Connor, the TV satirist who inspired Liz’s childhood self but fell into obscurity. Liz tries to help her by hiring her on TGS but finds Rosemary too out-of-touch.
Fisher (who had a prolific side gig as a script doctor) brings some of herself into the part. It’s also so clever that the episode uses Fisher (i.e., Liz’s fictional childhood hero, Leia) to play a character who represents who Liz wanted to be and a worst-case scenario of who she might become.
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Devin Meenan
Devin Meenan is a freelance entertainment writer. His first love was movies but he found himself writing more passionately about TV, hence him joining the Tell-Tale TV team. His favorite types of TV to sink into include prestige dramas, mystery box thrillers, sci-fi/fantasy, and anime.
