Allison Janney as Macy Smart

Bryan Cranston as Buddy Smart

Benjamin Evan Ainsworth as Lester Smart

Jack Champion as Derrick Smart

Simon Rex as Kyle

Chris Cooper as Walter

Laura Benanti as Tallulah Bankhead

Cady Huffman as Principal Franklin

Jessica Clement as Selena Roach

Ian Ho as Little Ricky

Mark Caven as Noël Coward

Chick Reid as Ruth Gordon

Doug Murray as Pastor Ellis

Colton Gobbo as Metalhead

Lindsay Leese as Loud Sue

Carolyn Scott as Fritzi

Madison Baines as Annabeth

Neil Whitely as Dr. Kannengiser

Darrin Baker as Principal Harris

David MacLean as William Inge

Michael Hanrahan as Ed Monroe

Allan MacAskill as Ernie Saracino

Houston Wong as 7/11 Clerk

Enzo Pellini as Lutheran Pastor

Parker Corno as Jock

Griffin MacIntyre as Metalhead 2

Daniel Kash as Tevye (Fiddler on the Roof)

Barbara Rajnovich as Golde (Fiddler on the Roof)

Allan Price as Lazar (Fiddler on the Roof)

Megan Byrne as Tzeitel (Fiddler on the Roof)

Emily Hawton as Chava (Fiddler on the Roof)

Dana Hodgson as Fyedka (Fiddler on the Roof)

Liam Culhane as Motel (Fiddler on the Roof)

Jude Evans as Male Hair Cast 1

Morgan Bedard as Male Hair Cast 2

Kelsey Ruhl as Female Hair Cast 1

Kaitlyn Stewart as Female Hair Cast 2

Laurie Murdoch as Major General Stanley (Pirates of Penzance)

Christian Bellsmith as Pirate 2 (Pirates of Penzance)

Darryl Hinds as Pirate 3 (Pirates of Penzance)

Daniel Stolfi as Pirate 4 (Pirates of Penzance)

Bryn Kennedy as Daugher 1 (Pirates of Penzance)

Hallie Seline as Daugher 2 (Pirates of Penzance)

Andrea Ciacci as Daughter 3 (Pirates of Penzance)

Monica Dottor as Daughter 4 (Pirates of Penzance)

Paul Lemelin as Fiddler (Fiddler on the Roof)

David Klein as Young Man in Theatre