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- John Cusack as Adam Yates
- Rob Corddry as Lou Dorchen
- Craig Robinson as Nick Webber-Agnew
- Clark Duke as Jacob Yates/Dorchen
- Chevy Chase as Father Time/Hot Tub Repair Man
- Collette Wolfe as Kelly Yates/Dorchen
- Crispin Glover as Phil Wedmaier
- Sebastian Stan as Blaine
- Lizzy Caplan as April Drennan
- Crystal Lowe as Zoe
- Kellee Stewart as Courtney Agnew-Webber
- Lyndsy Fonseca as Jenny
- Charlie McDermott as Chaz
- Jessica Pare as Tara
- William Zabka as Rick Steelman
- Josh Heald as Terry