- Tracy Pollan - Kelly
- Kathie Lee Gifford - Self
- Justin Long - Zack
- Christopher Lloyd - Principal McTavish
- Peter Hermann - Jeremy
- Samantha Bee - Dr. Young
- Henriette Mantel - Mrs. Pochovitz
- Matt Lauer - Matt Lauer
- Savannah Guthrie - Savannah Guthrie
- Al Roker - Al Roker
- James Martinez - Mr. Diaz
- Yury Tsykun - Russian Delivery Guy 2
- Todd Barry - Security Guard
- Erika Woods - Attractive Woman
- Opal Alladin - Principal Lacey
- Steve French - Hockey Dad
- Shannon Walsh - Lisa Mitchel
- Victor Williams - Todd
- Jeffrey Omura - Ted
- Gwynneth Bensen - Prof. Young Woman
- Victor Cruz - Doorman
- Craig Bierko - Bill
- Jason Jones - Chaz Garrity
- Candice Bergen - Beth Henry
- Alice Kremelberg - Reese
- Jake Lacy - Scott
- Charles Grodin - Steve Henry
- Rob Delaney - Clete Matthews
- Sting - Sting
- Matt Braunger - Dennis
- Malcolm-Jamal Warner - Russell
- Colby Minifie - Margot
- Domenick Lombardozzi - Ted
- Dennis Staroselsky - Nikolai
- Tanner Flood - Jake
- David Furr - Andy
- Amir Darvish - Limo Driver
- Ali Wentworth - Trista
- Lyrica Okano - Caroline
- Frederick Weller - Will
- Peter Vack - Andreas
- Jason Kravits - Doug
- Anne Heche - Susan Rodriguez-Jones
- Scott Nicholson - Detective
- Richard Kind - Mr. Norwood
- Thedra Porter - Pageant Worker (uncredited)
- Jack Haley - Larry
- Vandit Bhatt - Kevin
- Gregory Abbey - Coach Greg
- Lance Kerfuffle - Businessman
- Brendan Burke - Cop 1
- Alan R. Rodriguez - Cop 2
- Jimmy Gary Jr. - Sanitation Worker
- David Boston - Bus Passenger (uncredited)
- Dwayne Clark - Singing Waiter #1
- Ali Ewoldt - Singing Waiter #2
- Derek Roché - Handsome Waiter
- Christopher Sears - Goth Guy
- Danielle K. Thomas - Elise
- Julia Tokarz - Singing Waiter #3
- Karen Walsh Rullman - Sylvia
- David Ebert - Guy
- Andrew Kaempfer - Drifter
- Jonathon Olivo - Horny High School Student (uncredited)
- Nicole Brydon Bloom - Amy
- Erik Heger - Gary
- Craig Bockhorn - Desk Clerk
- Sarah Moliski - Student (uncredited)
- Sarah Moliski - High School Student (uncredited)
- Brooks Brantly - Fan
- Alexander Jameson - Kid
- Lily Mercer - Woman
- Maximillian Stebelsky - Tiny Goaltender
- Maximillian Stebelsky - Aidan
- Peter Ashton Wise - Man
- Chris Christie - Governor Chris Christie
- Robert Peterpaul - Student (uncredited)
- Keith Webb - Student (uncredited)
- Quincy Chad - Athletic Guy #1
- Einar Gunn - Minister
- J.B. Adams - Chris
- Raquel Almazan - Cashier
- Tibor Feldman - Cabbie
- Ira Coleman - Ira
- Rob Mathes - Rob
- Emilio Delgado - Flower Vendor
- Jay Aubrey Jones - Priest
- Chris Jehnert - Cute Theatre Boy (uncredited)
- Joe Saulino - Hipster Bar Patron (uncredited)
- Ana Nogueira - Kay Costa
- Jackie Hoffman - Pageant Coordinator
- Tom Degnan - Handyman
- David Andrew MacDonald - Mark Farrell
- Rana Roy - Megan Cute Shoes
- Nikki Granatell - Dancer #3
- Kevin Carolan - Carnival Guesser
- Kimiye Corwin - Pedicurist
- Tim Intravia - Silver Man
- Rajeev Pahuja - Carnival Worker (uncredited)
- Ravi Patel - Ranesh
- Dorin Seymour - Mr. Reynolds
- Don Puglisi - Sweaty Seth
- Dared Wright - Tango Dancer (uncredited)
- Dylan Blue - Student
- Jill Shackner - Claire
- Odiseas Georgiadis - Andrew
- Emmy Laybourne - Robin
- Benjamin Koldyke - Brandon
- Yuval David - Yaron
- Kristina Reyes - Maria
- Sejal Shah - Stella
- Meaghan Monaghan - Cool Girl (uncredited)
- Matt Wood - Dan
- Wendey Stanzler
- Ken Whittingham
- Michael Patrick Jann
- Victor Nelli Jr.
- Greg Staley
- Alex Reid
- Kristen Lange
- Lon Zimmet
- Stephen Basilone
- Laura Kittrell
- Amy Aniobi
- Emily Cutler
- Michael J. Fox
- Charlotte Taylor
- Jerry Kupfer
- Clint Koltveit
- Tami Sagher
- Sam Laybourne
- Eric Harwood
- Jeff Cardoni
- Matt Decker
- Griffin Richardson
Michael J. Fox interpreta a Mike Henry en la serie.
Christopher Lloyd hace el papel de Principal McTavish.
Sting interpreta a Sting en la serie.
Betsy Brandt interpreta a Annie Henry en la serie.
Juliette Goglia interpreta a Eve Henry en la serie.
Conor Romero interpreta a Ian Henry en la serie.
Jack Gore hace el papel de Graham Henry.
Katie Finneran hace el papel de Leigh Henry.
Wendell Pierce interpreta a Harris Green en la serie.
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