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'30 Rock's' 30 best guest stars

When “30 Rock” rides into the sunset Jan. 31, viewers will be left with countless hilarious memories of the core cast — Tina Fey (Liz Lemon), Alec Baldwin (Jack Donaghy), Tracy Morgan (Tracy Jordan), Jane Krakowski (Jenna Maroney), Jack McBrayer (Kenneth Parcell) and all the behind-the-scenes talent of “TGS With Tracy Jordan.” But one of the most consistent reasons to love the series was
Chris Parnell, Oprah Winfrey and Will Arnett all guest starred on \"30 Rock.\"
Chris Parnell, Oprah Winfrey and Will Arnett all guest starred on \"30 Rock.\"Today

When “30 Rock” rides into the sunset Jan. 31, viewers will be left with countless hilarious memories of the core cast — Tina Fey (Liz Lemon), Alec Baldwin (Jack Donaghy), Tracy Morgan (Tracy Jordan), Jane Krakowski (Jenna Maroney), Jack McBrayer (Kenneth Parcell) and all the behind-the-scenes talent of “TGS With Tracy Jordan.” But one of the most consistent reasons to love the series was the diversity of its guest stars. Given the talent pool involved, everyone’s list of the 30 best “30 Rock” guests is likely to be different, but here are our picks in no particular order.

1. Ghostface Killah as himself (Season 1)

As the very first celebrity to play himself on “30 Rock,” the Wu-Tang Clan man rapped his way through Jenna Maroney’s episode-ending performance of “Muffin Top” and set the tone for the show’s slightly askew sensibilities when selecting guest stars.

2. Chris Parnell as Dr. Leo Spaceman (Seasons 1 – 7)

Although he now serves the greater good as the United States Surgeon General, Leo Spaceman spent much of “30 Rock’s” run offering medical advice of dubious merit to the cast and crew of “TGS.”  Although he is purportedly a graduate of the Ho Chi Minh City School of Medicine and appears in the Writers Guild Health Manual under fertility, meth addiction and child psychiatry, there are numerous reasons to suspect that the “Dr.” that appears before Spaceman’s name is in quotation marks, not least of which is his credo, “Science is whatever we want it to be!”

3. Dean Winters as Dennis Duffy (Seasons 1 – 7)

Liz Lemon’s longest-running ex-boyfriend consistently proved to be equal parts bad cold and bad penny, regularly lingering for extended periods of time and, after inevitably getting the boot from Liz, reappearing when his presence was neither requested nor desired. On the other hand, he briefly made beepers cool again and was semi-successful in turning the word “dummy” into a term of endearment, so he wasn’t without his merits.

4. Paul Reubens as Prince Gerhard Messerschmidt Ramstein Von Hap (Season 1)

In a 2011 GQ interview, Tina Fey described the episode featuring Reubens, who turns in a thoroughly disconcerting performance as an inbred Austrian prince who dies before the closing credits roll, as a pivotal one in the series’ history. “It was the last episode that we shot before we were supposed to get our (season 2) pick-up,” said Fey. “When we were on-set, we were joking that the episode was called ‘Black Tie’ but should be called ‘Good-bye, America!’”

5. Isabella Rossellini as Bianca Donaghy (Season 1)

During her all-too-brief two-episode stint as Jack Donaghy’s ex-wife, the “Blue Velvet” star’s gift of gravitas transformed the line “Dammit, Johnny, you know I love my Big Beef and Cheddar!” into comedy gold.

6. Will Arnett as Devon Banks (Season 1 – 7)

Jack Donaghy’s boss may have changed over the years, shifting from Don Geiss (Rip Torn) to Kathy Geiss (Marceline Hugot) to Hank Hooper (Ken Howard), but his nemesis has remained the same from start to finish. With a lust for both power and Kenneth Parcell, Devon Banks rarely missed an opportunity to try and gain any sort of advantage over Jack, shifting his allegiances at the drop of a hat if it would help him gain the upper hand. Sadly, it never does.

7. Elaine Stritch as Colleen Donaghy (Seasons 1 – 7)

It’s hard to say who suffered more in the mother/son relationship between Colleen and Jack, but from the character’s first appearance to her indisputably epic funeral, Colleen Donaghy proved to be one of TV’s funniest — and bitchiest — mothers.

8. Carrie Fisher as Rosemary Howard (Season 2)

Although Fisher gamely delivered the obligatory Princess Leia riff (“Help me, Liz Lemon, you’re my only hope”), as one of Liz’s comedy-writing heroes, her real role was to deliver a message about how comedy doesn’t always translate well from one generation to the next.

9. Paul Scheer as Donny Lawson (Season 2)

Jack isn’t the only “30 Rock” character with a nemesis: During season 2, Kenneth regularly tussled with fellow NBC page Donny. Alas, their “page-off” was broken up by Pete before a true victor could be declared.

10. David Schwimmer as Jared a.k.a. Greenzo (Season 2)

After “Friends” left the air in 2004, the actor formerly known as Ross Geller stepped away from the small screen in a big way, but he made a memorable one-off return to the world of sitcoms to play an in-your-face mascot for global warming awareness whose sudden success causes him to develop a planet-size ego.

11. Al Gore as himself (Seasons 2 and 4)

When Greenzo grew too big for his britches, Jack tried to trick the former vice president to step in, but other matters attracted his attention, necessitating a hasty departure. (“A whale is in trouble! I have to go!”) A few seasons later, Gore reappeared to assist the “TGS” offices in their effort to go green by switching out a few light bulbs and transforming a dirty snack table into a lush garden. As is only befitting for an environmentalist, Gore also recycled his “a whale is in trouble” exit line. While an admirable gesture, it was funnier the first time.

12. Buck Henry as Dick Lemon (Seasons 2 and 5)

Given “30 Rock’s” premise and its creators’ pedigree, it’s hardly surprising how many former “Saturday Night Live” cast members have turned up as guests. But Tina Fey added an extra touch of class by bringing in 10-time “SNL” host — and, lest we forget, co-creator of “Get Smart” and screenwriter of “The Graduate” — Buck Henry to play her dad.

13. Andy Richter as Mitch Lemon (Season 2)

In further family matters, Fey also scored points for having Conan O’Brien’s longtime sidekick play her brother, then giving the character a neurological disorder where he perpetually believes he’s in high school circa 1985. This afforded him the opportunity to use pick-up lines such as, “Do you like Wham? 'Cause I'm kinda like the George Michael of my school …”

14. Tim Conway as Bucky Bright (Season 2)

In another nod to her comedy roots, Fey called upon a star player from the ensemble of “The Carol Burnett Show” to play “a major TV star in the ‘40s, ‘50s and the fall of 1972” who turned out to be sexist, racist, anti-Semitic and several other unsavory adjectives.

15. Oprah Winfrey as herself … sort of (Season 3)

After washing down a couple of Comanaprosil (“may cause dizziness, sexual nightmares, and sleep crime”) with a mixed drink to help her get through a flight, Liz hallucinated that her seatmate was none other than Oprah Winfrey. When the drugs wore off, the illusion was shattered in a big way — “Oprah” turned out to be a sassy ‘tween named Pam who bore little resemblance to the talk-show queen.

16. Jennifer Aniston as Claire Harper (Season 3)

Adding another former “Friend” to their roster of guest stars, Aniston turned up on in season 3 as an old friend of Liz’s whose hobbies included non-stop partying and bleeding men dry. Of course some might argue that the more impressive guest-star turns in the episode, which was entitled “The One With the Cast of ‘Night Court,’ ” came courtesy of Harry Anderson, Markie Post and Charles Robinson.

17. Steve Martin as Gavin Volure (Season 3)

Martin played an eccentric and ostensibly agoraphobic businessman friend of Jack’s who fell for Liz, leading her to believe that she’d finally found the perfect anti-social soul mate. But he broke her heart when he revealed that he’s actually under house arrest for arson and fraud.

18. Peter Dinklage as Stewart (Season 3)

Although his stint playing one of Liz’s boyfriends was short — stop it! — the future “Game of Thrones” star nonetheless made a big impression in his one appearance.

19. Jon Hamm as Dr. Drew Baird (Seasons 3 to 5)

In a recurring role referred to by TV historians as “that time when the dude from ‘Mad Men’ showed everybody that he was both hot and hilarious,” Hamm played Liz’s pediatrician neighbor who, she soon discovered, was so unbelievably handsome that he would unconsciously manipulate everyone around him in order to live a life of perfection. Naturally, Liz popped the bubble in which he’d been residing, sending him into the real world, a place that ultimately led him to lose both his hands (one in a fireworks explosion, the other in a helicopter accident). Even handless, though, he’s still pretty hot.

20. Alan Alda as Milton Greene (Seasons 3 and 5)

After years of mystery about the identity of his biological father, Jack was horrified to learn that he shares DNA with Milton Greene, a decidedly liberal professor at Bennington College. Greene’s greatest moment on the show occurred when his failing kidney inspired Jack to hold a charity concert featuring a roster of performers including Clay Aiken, the Beastie Boys, Mary J. Blige, Sheryl Crow, Cyndi Lauper, Michael McDonald and many more. (It’s revealed a few seasons later that Elvis Costello, ever the soft touch, ended up giving Greene one of his kidneys.)

21. Jeff Dunham as Rick Wayne (Season 4)

Hipsters may not admit to enjoying Jeff Dunham’s ventriloquism act, but even the cool kids can appreciate his appearance on “30 Rock,” where his redneck dummy Bubba J — or Pumpkin, as he’s called in the episode — spewed a foul-mouthed tirade at Liz when she started heckling him. Pumpkin ended up getting a serious stomping from Jack … like, to the point of decapitation. Good times.

22. Buzz Aldrin as himself (Season 4)

In an effort to top his accomplishments as the lunar module pilot of Apollo 11, Aldrin turned up on “30 Rock,” where, as it turns out, he’d preceded his mission to the moon by being the first love of Liz Lemon’s mother, Margaret (Anita Gillette).

23. Matt Damon as Carol Burnett (Seasons 4 and 5)

No, not that Carol Burnett, silly. Damon played an airline captain who began a relationship with Liz that started out strong, but ended up falling apart when they realized that they’re both too stubborn for things to work out.

24. Elizabeth Banks as Avery Jessup (Seasons 4 to 6)

Jack’s list of former girlfriends is a mile long and includes a former secretary of state (Condoleeza Rice), an art dealer (Emily Mortimer), a Democratic congresswoman (Edie Falco), his mother’s nurse (Salma Hayek) and, of course, the inevitable high-school crush for whom he still harbors feelings (Julianne Moore). But the MVP of the bunch has to be conservative CNBC commentator Avery Jessup. That’s not because they ended up getting married and having a child together, but  because Elizabeth Banks had the longest stint of any of Jack’s romantic interests, and in turn delivered more laughs than any of the others.

25. Will Forte as Paul L'Astnamé (Seasons 4 to 7)

Although he first appeared on the show as a different character, Forte made his greatest impression as a Jenna Maroney impersonator who goes on to actually marry Jenna Maroney, and at Jack’s mother funeral, no less! (Accordingly, he takes both her first and last names.)

26. Michael Keaton (Season 5)

The star of “Night Shift,” “Mr. Mom” and “Multiplicity” hasn’t had nearly enough comedic roles in recent years, so it was a real treat to see him turn up on the series’ hour-long 100th episode spectacular as a maintenance man battling a gas leak at 30 Rock.

27. John Slattery as Steve Austin (Season 5)

After getting good returns from one “Mad Men” star, why not bring in another one? Slattery played a Rhode Island political candidate who had Jack Donaghy’s support until Jack realized the man was a complete nut job, with a platform revolving around a return to the Founding Fathers’ sensibilities, including unpaved roads and legalized slavery. Even then, Jack was so intent on seeing Regina Bookman (Queen Latifah) lose that he threw Austin a fundraiser anyway. Stay classy, Jack.

28. Weird Al Yankovic as himself (Season 6)

Jenna entered into a feud with Al when he parodied one of her songs, inspiring her to team up with Tracy and write a new track that would prove impossible to parody. But the end result sounded so ridiculous that Al responded by turning it into a serious song, which infuriated her further.

29 and 30. Bryan Cranston and Catherine O’Hara as Ron and Pearline (Season 7)

Some couplings are just too strong to separate, so we’re closing with a twofer and letting these “Breaking Bad” and “SCTV” icons share the spotlight as Kenneth’s mom, Pearline, and her “friend” Ron, who turns out to have been Kenneth’s stepfather for the past seven years. The real highlight  is the short but oh-so-sweet duet between Cranston and O’Hara. It just doesn’t get any better than that. 

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