Season 5
16 episodes · Feb 27, 2006
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- S5E2
The Razor's Edge
Mar 6, 2006The candidates challenge New Yorkers to text message on their mobile phones.
S5E3Get it in Gear
Mar 13, 2006The candidates must throw a corporate retreat for car-dealership owners.

S5E5Cruise Control
Mar 27, 2006The remaining candidates must create a new commercial for Norwegian Cruise Lines. Project
S5E6King of the Jingle
Apr 3, 2006The twelve remaining candidates are challenged to write an advertising jingle for Arby's.
S5E7It's More Than D'Cor
Apr 10, 2006The eleven remaining candidates are assigned to create activity areas to benefit a children's charity in a renovation-themed task.
S5E8A Slice Of Heaven
Apr 10, 2006The remaining candidates launch a new pizza sandwich for 7-Eleven.

S5E10Assault on Battery
Apr 24, 2006Trump's children, Ivanka and Donald Jr. fill in for Carolyn and George for this task, which requires the remaining candidates to promote one of New York City's biggest tourist attractions.
S5E11Blow Out
May 1, 2006Trump's children, Ivanka and Donald Jr. fill in for Carolyn and George for this task, which requires the remaining candidates to promote one of New York City's biggest tourist attractions.
S5E12Back to School
May 8, 2006And then there were eight. The candidates dive into a hair-raising challenge in which they must oversee the grand openings of two hair salons.
S5E13Backs against the Wal-Mart
May 15, 2006The remaining candidates tackle a challenge to throw a tailgate party at a college football game, with one team cooking up plans for an eating contest.
- S5E14
Who Wears The Pants
May 22, 2006The remaining five candidates must create a store display for the new Xbox 360 at Wal-Mart. Real life meets reel life for the winners when they jet off to the West Coast to meet film executive Jeffrey Katzenberg, who gives them an opportunity to participate in a voiceover session for the animated movie Over the Hedge.
S5E15The Final Battle
May 29, 2006The remaining four candidates are tasked with creating a new line of uniforms for an upscale hotel chain. The winners then enjoy some time out on the town.
- S5E16
Season Finale
Jun 5, 2006The final two candidates are challenged to coordinate two high-profile charity events.