Special Guest Stars Jon Hamm as Richard Wayne Gary Wayne Guest Stars Sara Chase as Cyndee Pokorny Michael Carlsen as Mikey Politano Peter Riegert as Artie Goodman Greg Kinnear as Himself Co Starring Noah Robbins as Zach Elise Mestichelli as C.H.E.R.Y./L. Jonathan Braylock as Banana Boy B James Hosey as Tyler Stephanie D'Abruzzo as Puppeteer Robert Lenzi as Wall Street Bro Michael Joseph Murray as Doorman #2 Dylan Prince as Young Nerd Niloy Alam as Kabir Frank Ward as Doorman Kara Rosella as Russian Woman