The Best Episodes of Undercover Boss Season 5

Episode Rankings

1. #1 Fan Favorite
   

   6.0/10(61 votes)

   #1 - 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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2. 

   6.0/10(42 votes)

   #2 - 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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3. 

   6.8/10(42 votes)

   #3 - 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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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. 

   6.9/10(39 votes)

   #5 - 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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6. 

   6.8/10(32 votes)

   #6 - 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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7. 

   7.0/10(37 votes)

   #7 - 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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8. 

   7.3/10(33 votes)

   #8 - 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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9. 

   6.5/10(29 votes)

   #9 - 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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10. 

    4.6/10(33 votes)

    #10 - 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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11. 

    7.5/10(31 votes)

    #11 - Mohegan Sun Casino

    S5:E111/17/2014

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

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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. 

    7.0/10(29 votes)

    #13 - 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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14. 

    7.2/10(24 votes)

    #14 - 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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15. 

    7.4/10(29 votes)

    #15 - 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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