Special Guest Stars Michael Rapaport as Leonard Amy Sedaris as Flora Guest Stars Yamaneika Saunders as Maya Sas Goldberg as Jess Laura Benanti as Jane Jones Arielle Siegel as Jen LaVar Walker as LaVar Kevin Kane as Matt Rosebud Baker as Meri Gary Gulman as Shlomo Lily Fisher as Young Ann Charlie Hall as Officer Beau Dave Attell as Rabbi Jimmy Buffett as Busker Big Freedia as Himself Co Starring D.C. Benny as Bart Wallace Mia Jackson as Denisha Benjamin Jaffe as Ben Kenneth Dion Johnson as Charles Rosha Washington as Joe Joe Charles Gabriel as Himself (Charlie Gabriel) Joule Lee as TBD Crosby Miner Peltz as TBD Steve Rapport as Caricature Artist Azalea Sylvie Rufo as Singing Girl Uptown T as Himself