Over a decade after its heyday, Must See TV and its inextricable herd of guest stars triggers groans, nostalgia, or a mix both. Way too often, a guest star stint is a clear bit of ratings bait, offering little to no comedic value other than a distracting applause track when a “big name star” makes their entrance. Friends was plenty guilty of this type of stunt casting (I legitimately used to think “The One After the Superbowl” was named “The One with Julia Roberts and Brooke Shields”, probably because that’s a way more evergreen title), but it also had a great deal of gems, where star power and legitimate comic ability created truly memorable, oddball characters. After the cut is a list of my top 10 Friends guest star stints.

10. Teri Garr as Phoebe Abbott Sr.

The Friends casting directors were at their best when casting family members, and Teri Garr as Phoebe Sr. is a pitch perfect example. Kooky, subdued, and almost a little sad, Garr’s performance lends some wonderful depth to Phoebe’s ongoing mission to explore any family she can find. The similarities between Garr and Kudrow are obvious to anyone (with the exception of the actresses themselves, at least according to this retrospective), and their scenes together are a signature mix of sincerity and quirkiness that came to define Friends at its finest moments.

Best moment:

In trying to warn Phoebe how difficult it is to give up a child, Phoebe Sr. realizes her strategic misstep a minute too late:

9. Gary Oldman as Richard Crosby

If Gary Oldman traded every Red Righting Hood and Paranoia role and instead spent more time playing Oscar losers with excellent elocution, I think we’d all be a little happier. Having a struggling actor for a main character creates an easy excuse for guest star roles, and over the years Friends had a lot of fun with Joey’s brushes with fame. We’re talking about a character who got caught using Charlton Heston’s shower, and peed on (or near) Jeff Goldblum. Oldman’s amiable British thespian is far and away the most fun of these story lines. He commits so fully to the silliness of these B-plots that it would be easy to forgive extraneous scenes, but the writers deserve credit for tying Oldman’s character into an overarching  plot and turning him into an obstacle for one of the major events of the series: Monica and Chandler’s wedding.

Best moment:

Both of his episodes are so amusing it’s tempting to just list them both, but his theatrical spitting gets edged out ever so slightly by “Is that my ass?” The genuine confusion of the delivery is what settled it for me:

8. Brad Pitt as Will Colbert

Brad Pitt’s formerly fat Rachel hater usually tops these lists, and for generally good reason. His appearance on Season 8’s thanksgiving episode is fun, funny, and give us more backstory on the Long Island adolescence of Rachel, Monica, and Ross.  If we’re being perfectly honest with ourselves, it does have to be said that the humor relies a little too much on the “joke” that Jennifer Aniston’s then-husband hates her guts in the show, and I’m not so sure he would be the perennial favorite guest star if that weren’t the case. Nevertheless, Will’s seething hatred, still going strong some 15 years after high school, is too delightfully over the top not to include on the list.

Best moment:

Pitt nails the bitchy hair toss (at the 4:40 mark) so well, I can’t imagine picking anything else:

7. Marlo Thomas as Sandra Green

Like Will Colbert, this is another case where external knowledge of the guest star informs the comedy behind their character. Placing the iconic Marlo Thomas as Rachel’s mom winks at the audience’s knowledge of pop culture history, inviting them to make the obvious comparison between That Girl‘s Ann Marie and Rachel Green, her modern day counterpart. Unlike the Brad Pitt stint, however, the writers use this background knowledge as a diving board, rather than a static joke. Thomas is not Ann Marie all grown up. Instead, she’s a wealthy housewife whose never had to work, and ironically now finds herself jealous of her daughter’s empowered life as a part time Central Perk waitress. Especially in her first appearance, Sandra Green provides a wonderful, subtle deconstruction of the glamour behind the “working woman” characters she herself helped pioneer.

Best moment: Sandra’s constant bitchiness towards Monica for forgetting to invite her to Rachel’s baby shower is a work of passive aggressive art only a mother could hope to create. But since I can’t find a video of that, have this instead:

6. Alec Baldwin as Parker (a.k.a Santa Clause on Prozac at Disney Land, Getting Laid)

This one’s just plain fun.  Alec Baldwin’s Parker is serial killer levels of enthusiastic, teetering from endearing to excruciating. I could rationalize his placement on this list by critically analyzing how Parker’s cartoonish positivity helps Phoebe become a more nuanced character by comparison, highlighting her darker personality traits. But I’m not going to because Alec Baldwin knocked this happy weirdo so out of the park, nothing else needs to be said.  Just a plain, simple, perfectly done guest spot. I must take a mental picture of it all.

Best moment:

The above quote, as well as force feeding Phoebe oysters that “look too weird”:

5. Giovanni Ribisi as Frank Buffay Jr.

Phoebe’s protectiveness over her baby brother is one of the most touching continuous story lines of the show, pairing high stakes emotional plot points with an overarching weirdness. Ribisi is really the only choice for Frank Jr., a high school senior who looks like an insomniac in his late twenties but acts like a 13 year old kid. For all of his ickiness, Frank Jr. is possibly the sweetest, most optimistic guy in the show’s cast of recurring characters, happily pursuing his dreams whenever we run into him. That those dreams consist of marrying Debra Jo Rupp and attending refrigerator college makes him ever sweeter.

Best moment:

No contest- this (allegedly improvised) line from The One With the Embryos is one of the most memorable deliveries in the show’s history:

4. Hank Azaria as David The Scientist Guy

David appeared only in 5 episodes spread out over 3 seasons,  but the character’s meek sweetness is memorable enough to make him feel like one of the show’s more important stars. Compare David to Mark, Rachel’s Bloomingdale’s coworker, who appeared in 6 episodes and factored into one of the show’s defining storylines and yet is remarkably insignificant on rewatch. Azaria plays David with a great understated quirkiness that perfectly compliments Kudrow’s performance in the early seasons, and it’s easy to imagine these two living happily ever after. More than any other character, Phoebe often dealt with bittersweet love stories, but David’s meek romantic scientist is the only one who legitimately feels like the one who got away.

Best moment:

I’m partial to David’s introduction, wherein Phoebe yells at him for talking during her performance and he proceeds to charm her in a bumbly awkward manner. Can’t find a video of that exchange, so I’ll type it up:

David: I was just saying to my friend that I thought you were the most beautiful woman that I’d ever seen in, in my life. And then he said that-you said that you thought Daryl Hannah was the most beautiful woman that he’d ever seen in his life, and I said “Yeah, I liked her in Splash a lot but not so much in, in Wall Street, I thought she had kind of a hard quality” and that, and that uh while Daryl Hannah is beautiful in a conventional way, you are, uh, luminous with kind of a delicate grace. Then, uh, that’s, that’s when you started yelling.

David’s final return from Minsk is equally sweet:

3. Adam Goldbeg as Eddie Menuek

This guy. What the fuck even was he? God bless. Eddie’s run is buried in season two and never gets mentioned again, but his few episodes are some of the most entertaining–and bewildering. For longer than I care to admit, I thought that Adam Goldberg and Michael Imperioli were one and the same, and Chandler’s manic temporary roommate was also Christopher Moltisanti. I still like to pretend that’s the case, but Goldberg’s intense fruit drying psychopath is a pleasure to watch all on his own.

Best moment:

The day after Chandler begs him to move out, Eddie describes the crazy fun night he had with Mr. 21 over here.

This moment’s up there as well:

2. Bruce Willis as Paul Stevens

Much like Baldwin’s stint, Bruce Willis’ Paul Stevens is an example of a guest star doing everything right. Coming off of the Sixth Sense, Willis enthusiastically throws himself into the role of Elizabeth’s terrifying, handsome father. It’s a clever bit of comedy casting that revels in the actor’s status as one of the most intimidating leading men for only an episode before  gradually shedding layers way to reveal a puddle of a man who gives himself mirror pep talks and cries all over Rachel’s lap. It’s clear the cast is loving these scenes, and that joy becomes infectious.

Best moment:

Duh.

1. Elliott Gould and Christina Pickles as Jack and Judy Geller

Friends was a huge show, and as its ratings blew up it attracted a large amount of big name stars. But none compare to the Season 1 coup of getting Elliott Gould and Christina Pickles to play Monica and Ross’s well-meaning but judgmental parents. The pair appears as early as the second episode, and are featured in all ten seasons. Their often inappropriate appearances are always a welcome surprise to the audience, if not their kids. Gould in particular brings a peculiar charisma to Jack, who manages to juggle a clear affection for his children with a constant bemusement. Pickles’ Judy is a bit tougher as the commanding hypercritical mother, but she colors the role with enough joy and softness to avoid a cliche depiction, and instead creates a believable mom to the neurotic Monica and Ross. Friends is at its best when it explores the formation of this non-nuclear family, and in that sense it’s impossible not to think of  Jack and Judy as the aloof grandparents. Though it’s also tough to think of those grandparents groping each other quite as often as they do, but that’s Monica’s problem, not ours.

Best moments:

Judy: After every single Friend breaks down one after another, Judy takes control.

Jack: Plenty of smaller moments come to mind, like drinking a can of condensed milk or forgetting about Ben’s existence or yelling “Now I’m depressed!” when his team loses during his mother-in-law’s wake. But since the internet is a cruel place where a compilation “Best of Jack Gellar” video isn’t readily available, I’ll also add this silly, sitcom-y moment:

You Deserved Better:  Aisha Tyler as Charlie Wheeler

Refreshing as it was to see a competent, intelligent, academic woman on the show, Aisha Tyler’s run as Ross’s love interest feels like a huge missed opportunity. Tyler is personable and hilarious, but you wouldn’t know it from this role alone, where she’s used only to throw a needless wrench into what was already a love triangle nobody wanted to see. I wish we could have seen less of one-note Charlie, and more of this Aisha Tyler: