Dianne Wiest Joan Actor James Brolin John Actor Zoe Lister Jones Jen Actor Colin Hanks Greg Actor Angelique Cabral Colleen Actor Thomas Sadoski Matt Actor Betsy Brandt Heather Actor Dan Bakkedahl Tim Actor Niall Cunningham Tyler Actor Holly J. Barrett Samantha Actor Giselle Eisenberg Sophia Actor Hunter King Clementine Actor Richard Marx Buddy Daiquiri Guest Star Leslie Jordan Neils Guest Star Todd Sherry Clancy Guest Star Mark Beltzman Max Guest Star Tatiana Carr Receptionist Guest Star Frank Crim Art Sturgeon Guest Star Nikiva Dionne Nurse Guest Star Michael Lanahan Dr. Nopunn Guest Star Robert Michael Lee Salesman Guest Star Fatimah Taliah Fire Marshal Mull Guest Star Rosalie Vega Tanya Guest Star Justin Adler Executive Producer Aaron Kaplan Executive Producer Jason Winer Executive Producer Jeffrey Morton Executive Producer Barbie Feldman Writer Jude Weng Director