The Best Episodes of Undercover Boss Season 5

Episode Rankings

1. #1 Fan Favorite
   

   7.5/10(31 votes)

   #1 - Mohegan Sun Casino

   S5:E111/17/2014

   Mohegan Sun Chairman Bruce "Two Dogs" Bozsum goes under cover.

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2. 

   7.4/10(29 votes)

   #2 - Sky Zone

   S5:E153/14/2014

   Jeff Platt, CEO of Sky Zone, the world’s first indoor trampoline park, jumps into action as a referee for a children’s dodgeball game. On another assignment, the 29-year-old boss – the youngest in the show’s history – has trouble hiding his in-depth knowledge of the company when working in community relations.

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3. 

   7.3/10(33 votes)

   #3 - Dutch Bros. Coffee

   S5:E811/15/2013

   Dutch Bros. Coffee co-founder and president Travis Boersma works under cover on a coffee plantation in El Salvador.

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4. 

   7.2/10(43 votes)

   #4 - Buffets, Inc.

   S5:E410/18/2013

   Buffets, Inc. CEO Anthony Wedo encounters an employee with a nasty attitude and learns how to work the grill station while he is undercover.

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5. 

   7.2/10(24 votes)

   #5 - Undercover Employee

   S5:E143/7/2014

   For the first time on UNDERCOVER BOSS, three previously featured bosses - Amit Kleinberger, CEO of Menchie's; Randy Dewitt, Co-Founder and CEO of Twin Peaks; and Steve Greenbaum, CEO and Co-Founder of PostNet - send an employee undercover for a second look inside their companies.

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6. 

   7.0/10(39 votes)

   #6 - Family Dollar

   S5:E711/8/2013

   Mike Bloom, President and COO of Family Dollar Stores, one of the largest discount retail companies in the country, faces his fear of heights when learning to operate a forklift that takes him 35 feet into the air. Also, the boss nearly blows his rock 'n' roll disguise when one employee invites him to a jam session.

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7. 

   7.0/10(29 votes)

   #7 - Utah Jazz

   S5:E132/28/2014

   Greg Miller, CEO of the Utah Jazz, one of the most recognizable basketball organizations in the NBA, attempts to make halftime history when he works undercover with their infamous Dunk Team. Also, the boss' team spirit is put to the test when he is asked to become a human basketball hoop as a member of the Interactive Team.

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8. 

   6.9/10(40 votes)

   #8 - Menchie's

   S5:E510/25/2013

   Menchie's frozen yogurt franchise CEO Amit Kleinberger goes undercover at a dairy farm and a kids birthday party.

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9. 

   6.8/10(42 votes)

   #9 - Donato's

   S5:E310/11/2013

   Donato's Chairwoman Jane Grote Abell goes under cover and discovers that pizza isn't the only thing getting baked at one store.

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10. 

    6.8/10(32 votes)

    #10 - Alfred Angelo

    S5:E611/1/2013

    Paul Quentel, President of Alfred Angelo, one of the largest bridal retailers in the U.S., is inspired after working with a hard-working, hearing impaired employee. Also, the boss isn't afraid to get in touch with his feminine side as he helps brides find their perfect wedding dress.

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11. 

    6.5/10(29 votes)

    #11 - Undercover Boss: Busted!

    S5:E911/22/2013

    Seven previously featured "Bosses" discuss the challenges they had with keeping their identity undercover. Also, they provide updates on some of their memorable employees.

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12. 

    6.3/10(25 votes)

    #12 - Hudson Group

    S5:E121/31/2014

    Hudson Group CEO Joe DiDomizio goes on an undercover mission.

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13. 

    6.0/10(62 votes)

    #13 - Twin Peaks

    S5:E19/27/2013

    Twin Peaks CEO Randy Dewitt goes under cover at the sports bar and grill chain, with the help of franchise owner -- and "Undercover Boss" alum -- Coby Brooks.

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14. 

    6.0/10(42 votes)

    #14 - Loehmann's

    S5:E210/4/2013

    When Loehmann's CEO Steven Newman goes under cover, he feels uncomfortable helping female customers shop for undergarments.

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15. 

    4.8/10(34 votes)

    #15 - Massage Heights

    S5:E1012/13/2013

    Massage Heights COO Shane Evans must overcome her aversion to touching other people when she goes under cover.

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