Recurring
Janet Varney as Becca Barbara (née Cottumaccio), Lindsay's sister and Jimmy's ex-girlfriend.
Todd Robert Anderson as Vernon Barbara, Lindsay's brother-in-law and Becca's immature husband. Vernon is an orthopedic surgeon who "performs hip replacements for old ladies".
Allan McLeod as Paul Jillian, Lindsay's independently wealthy ex-husband. Officially, Paul works for a bank as "Executive Vice President of Wealth Management", but he seems to have no duties to take up his time.
Shane Francis Smith as Killian Mounce, Jimmy and Edgar's pre-teen neighbor.
Brandon Mychal Smith as Sam Dresden, Gretchen's main client. Sam leads a rap trio and projects a "street" image, but his tastes run to Craft Movement furniture and fittings.
Darrell Britt-Gibson as Shitstain, a member of Sam's rap trio and his friend. His real name is Dale.
Colin Campbell as "Barfly", often seen drinking when the action takes place in a bar.
Giovonnie Samuels as Brianna (season 1), Gretchen's assistant at the PR agency.
Stephen Schneider as Ty Wyland (season 1–2, 4), a movie director who was Gretchen's lover before she met Jimmy, and who occasionally attempts to re-insert himself in her life, to Jimmy's dismay.
Allen Maldonado as Honeynutz (season 1–3), another friend of Sam and a member of his rap trio. His real name is Zachary. In season 4, it is revealed that Honeynutz is 45 years old, which causes Sam and Shitstain to dismiss him from the trio.
Steve Agee as Dutch (seasons 1–5), a character who misinterprets a chance remark as an invitation to abandon his current job and begin a new venture.
Mageina Tovah as Amy Cadingle (season 2), Paul's friend.
Tessa Ferrer as Nina Keune (season 2), former champion skier and owner of Jimmy's favorite bar.
Collette Wolfe as Dorothy Durwood (season 2–3), a member of Edgar's improv comedy troupe.
Kathleen Rose Perkins as Priscilla (seasons 3–4), a stylist who hires Lindsay as her assistant.
Doug Benson as himself (seasons 3–5); Edgar begins working for him as a sketch writer.
Samira Wiley as Justina Jordan (season 3 and 5), Gretchen's therapist.
Colin Ferguson as Boone (season 4), friend of Ty's who also befriends Gretchen.
Anne Dudek as Whitney, Boone's ex-wife. (season 4)
Brendan Jennings as Neil (season 4), Whitney's current husband, who is bullied mercilessly by Boone.
Johnny Pemberton as Max (season 4), a fellow sketch writer for Doug Benson and Edgar's new work friend.
Phil Abrams as Steeb Corniglia, the pretentious host of the in-show Wait Wait...Don't Tell Me! parody Tip of My Tongue (season 1 and 4).
JoNell Kennedy as Yvette (season 5), Gretchen's boss.
Brandon Black as Honeynutz 2 (season 5), replacing Maldonado in the trio.
Lou Taylor Pucci as Nock Nock (season 5), a rapper
