NOTE: When it comes to Web Therapy's illustrious guest stars, there are no weak links. This ranking reflects personal enjoyment, as well as what the actor and character brought to the series.
30. Rashida Jones
Character: Hayley Feldman-Tate
Seasons: 1 and 2
Rashida Jones is always charming, but it's hard to compete with Dan Bucatinsky as her husband Jerome, especially since her screentime has been reduced to accommodate Jones' busy schedule.
29. Selma Blair
Character: Tammy Hines
Season: 2
As Jerome and Hayley's trashy surrogate, Selma Blair was suitably messy. She didn't leave as lasting an impression as other guest stars, but her giant pregnant belly is hard to forget.
28. Maulik Pancholy
Character: Kamal Prakash
Season: 1
Maulik Pancholy had a fairly sizable part in the first season, working alongside Fiona and romancing Gina. In some ways, Kamal was a similar role to what Pancholy had done so well on 30 Rock.
27. Sara Gilbert
Character: Sylvie Frank
Season: 3
Sara Gilbert is perfect as the slight but menacing Sylvie. Her crush on a co-worker seems innocent at first, but Gilbert's deadpan reflects the more than a little unbalanced stalker underneath.
26. Courteney Cox
Character: Serena Duvall
Season: 1
Courteney Cox took part in Web Therapy's first Friends reunion, and for that, we'll always be grateful. Her psychic Serena was almost as delusional as web therapist Fiona, a difficult feat to accomplish.
25. Chelsea Handler
Character: Chris Endicott
Season: 3
Chelsea Handler plays Fiona's ex-husband post-gender reassignment surgery. Chris isn't the most memorable character, but Handler is game for just about anything, and she throws herself into the role.
24. Mae Whitman
Character: Blair Yellin
Season: 1
Her? Really, though, Mae Whitman is a solid addition to any show, and her pairing with Darren Criss on Web Therapy made for one of the most entertaining (and millennial-savvy) storylines this season.
23. Darren Criss
Character: Augie Sayles
Season: 3
As the other half of the Augie-Blair romance, Darren Criss is just as delightful as Mae Whitman. He earns one slot above her by playing against type here: Who knew Glee's Blaine could be such a stinky straight boy?
22. Victor Garber
Character: Kip Wallice
Seasons: 1, 2, and 3
Kip is an integral part of Web Therapy, and Victor Garber is great (as always) in the role. The only reason he's not higher up is that most of his time is spent as straight man (irony alert) to Fiona.
21. Alan Cumming
Character: Austen Clarke
Seasons: 1, 2, and 3
Like Kip, Austen Clarke is an essential figure in Fiona's life. Alan Cumming is well suited to the role of an eccentric billionaire. If anything, he could stand to be a little weirder — this is Alan Cumming after all.
20. Steven Weber
Character: Robert Lachman
Season: 1
No one is better than Steven Weber at going from calm and collected to completely losing his shit. He's a little more subdued here than he was in the TV movie version of The Shining, but Robert Lachman is still intense.
19. Bob Balaban
Character: Ted Mitchell
Season: 1
Like all therapists, Bob Balaban's Ted Mitchell is a little bit crazy himself. Balaban has never not been amazing in something, so even explaining why he's so good feels irrelevant. He's Bob Balaban!
18. Matt LeBlanc
Character: Nick Jericho
Season: 3
Another Friends reunion — Web Therapy is too good to us. Matt LeBlanc is equal parts handsome and distressing as a serious gambling addict. It's always nice to see him playing sharper than Joey but still damaged.
17. Meg Ryan
Character: Karen Sharpe
Season: 3
We don't see enough of Meg Ryan these days, so it was a pleasant surprise to see her turn up this season as a hoarder weirdly obsessed with Kip Wallice. Ryan is still cute, even when she's playing a little... off.
16. Rosie O'Donnell
Character: Maxine DeMaine
Season: 2
It's easy to forget that Rosie O'Donnell remains a very talented comedic actor, and her work on Web Therapy is a great reminder. Maxine is blunt, but she's also so strange — and we love when Rosie's weird.
15. Minnie Driver
Character: Allegra Favreau
Season: 2
Minnie Driver is so funny as a recovering alcoholic who Fiona sends over the deep end. (Dr. Wallice is not so great with addicts, is she?) Driver's Allegra is great when she's sober and when she's very much not.
14. Jane Lynch
Character: Claire Dudek
Season: 1
We know Jane Lynch can be scary, but her absurd aggression on Web Therapy is funnier than anything she's done on Glee. She's not just a bully with a heart of gold — she's actually insane.
13. Molly Shannon
Character: Kirsten Noble
Season: 2
Molly Shannon is adept at playing weirdos, and Kirsten is definitely that. Her strange obsession with Fiona and her Photoshop skills make her a compelling character for Shannon to play with.
12. Tim Bagley
Character: Richard Pratt
Seasons: 1, 2, and 3
Poor Richard. He suffers a lot on Web Therapy, and Tim Bagley captures that perfectly, whether he's whispering for fear of being heard by his wife, or just crying over Fiona at his desk.
11. Conan O'Brien
Character: Conan O'Brien
Season: 2
It's hard to say what was funnier about Conan's appearance – that he was playing himself, or that Fiona had no idea who he was. Either way, his barely repressed jealousy over Andy Richter made for great television.
10. Julia Louis-Dreyfus
Character: Shevaun Haig
Season: 2
Hey, it's another reunion — not of Friends, but at least of '90s sitcom stars. And Julia Louis-Dreyfus manages to be a solid adversary for Fiona as her sister Shevaun. It's a pleasure watching her lose her cool.
9. Michael McDonald
Character: Ben Tomlund
Seasons: 2 and 3
Kip's campaign manager turned boyfriend is one of Web Therapy's greatest villains. Michael McDonald is always funny, whether he's in his conservative attire or feeling slightly less inhibited.
8. Megan Mullally
Character: Franny Marshall
Season: 3
Boozy songwriter Franny is such a Megan Mullally part, it's difficult to imagine anyone else doing her justice. And of course, the role requires that Franny sing, as all great Mullally roles should.
7. Steve Carell
Character: Jackson Pickett
Season: 3
Before we knew Jackson was full of shit, Steve Carell came on very strong, enough that even those into Carell's new silver fox identity were still a little weirded out. He's been the greatest addition to this season.
6. David Schwimmer
Character: Newell Miller
Season: 2
Finally, the best Friends reunion of the bunch — David Schwimmer's turn as sad, creepy Newell was fantastic. It's like if Ross never found Rachel or dinosaurs. He's just... so lame, in the most entertaining way possible.
5. Julie Claire
Character: Robin Griner
Seasons: 1, 2, and 3
Sorry, Ben. Web Therapy's best villain is Robin, portrayed brilliantly by Julie Claire. She's so sharp and mean, often in a way that gets past Fiona, which is immensely satisfying to watch.
4. Dan Bucatinsky
Character: Jerome Sokoloff
Seasons: 1, 2, and 3
Outside of Lisa Kudrow, Dan Bucatinsky is the closest thing Web Therapy has to a regular cast member. Jerome is the perfect Bucatinsky character, which makes sense since Bucatinsky helped create him. He's a great neurotic.
3. Meryl Streep
Character: Camilla Bowner
Season: 2
It's Meryl fucking Streep, y'all. Obviously she can do no wrong, but she's especially fab as the conversion therapist working to turn Kip straight. She's so bright and sunny and evil!
2. Jennifer Elise Cox
Character: Gina Spinks
Seasons: 1, 2, and 3
Jennifer Elise Cox has always been hilarious, but she's been a character actor for too long. This woman is incredible, and so consistently funny as shockingly stupid Gina on Web Therapy. It's hard to imagine the show working without her.
1. Lily Tomlin
Character: Putsy Hodge
Seasons: 1, 2, and 3
All hail the queen. Lily Tomlin has always been amazing, and she will continue to be amazing forever, probably. As Putsy, she's able to show so much range — and so many costumes. It's the ideal venue for her endless comedic talents.