Undercover Boss (US)

10 Best Episodes of Undercover Boss (US) - Season 5

Undercover Boss (US) is an American adaptation of the British series of the same name. The show was first aired on CBS in 2010 and has since had 12 seasons. The premise of the show involves high-level corporate execs leaving their offices to take on low-level jobs in their companies to learn how things really work. Through this process, they learn things about their companies, their employees, and maybe even something about themselves. Here we will be ranking the best episodes of Undercover Boss (US).

Each episode of the show follows a different executive as they embark on their undercover mission. The show is well known for its dramatic endings, as the execs reveal themselves to their employees and often reward them with promotions, raises, and other rewards. From the 12 seasons of the show, some episodes have been more memorable than others.

Let's take a look at the best episodes of Undercover Boss (US). We'll rank the top episodes based on their impact, the drama of the reveals, and the messages of the show. These episodes have left a lasting impression and will be remembered for years to come.

Written by Sophie and last updated on feb 13, 2023.

PS: The following content contains spoilers!

PPS: I will admit that parts of this page was written with the help of AI - it makes my work so much easier to not start from a blank page!

Undercover Boss (US) - S5E14

#15 - Undercover Employee (Season 5 - Episode 14)

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.

The episode was rated 6.64 from 36 votes.

Undercover Boss (US) - S5E8

#14 - Dutch Bros. Coffee (Season 5 - Episode 8)


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

The episode was rated 7.15 from 41 votes.

Undercover Boss (US) - S5E2

#13 - Loehmann's (Season 5 - Episode 2)

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

The episode was rated 7.38 from 42 votes.

Undercover Boss (US) - S5E12

#12 - Hudson Group (Season 5 - Episode 12)


Hudson Group CEO Joe DiDomizio goes on an undercover mission.

The episode was rated 7.41 from 32 votes.

Undercover Boss (US) - S5E7

#11 - Family Dollar (Season 5 - Episode 7)

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.

The episode was rated 7.44 from 41 votes.

Undercover Boss (US) - S5E13

#10 - Utah Jazz (Season 5 - Episode 13)


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.

The episode was rated 7.44 from 34 votes.

Undercover Boss (US) - S5E5

#9 - Menchie's (Season 5 - Episode 5)

In this episode of Undercover Boss, CEO Amit Kleinberger of Menchie's frozen yogurt franchise goes undercover to find out what his customers really think. He starts his undercover mission on a dairy farm, where he learns the ins and outs of the business and interacts with the employees. Kleinberger is amazed by the hard work and dedication of the employees and gains a newfound appreciation for their commitment to the business.

Kleinberger then goes undercover at a kids' birthday party, where he gets to experience first-hand what it's like to serve customers as a Menchie's employee. He takes orders, serves up frozen yogurt, and even helps to clean up the mess afterwards. In the end, Kleinberger is able to see how his customers view the product and service and can make changes to the franchise accordingly.

The episode was rated 7.68 from 44 votes.

Undercover Boss (US) - S5E6

#8 - Alfred Angelo (Season 5 - Episode 6)


Paul Quentel, President of Alfred Angelo, the largest bridal retailer in the U.S., goes undercover in his own company in the episode of Undercover Boss (US). He is inspired by one of his hard-working, hearing impaired employee and takes the opportunity to get in touch with his feminine side to help brides find their perfect wedding dress.

Paul Quentel had a very memorable experience while undercover. He was truly moved by the dedication of his hearing impaired employee, who worked hard and proved to be an invaluable asset to their company. He also got to experience the joy of helping brides find their perfect dress, a moment that will stay with him forever.

The episode was rated 7.71 from 35 votes.

Undercover Boss (US) - S5E15

#7 - Sky Zone (Season 5 - Episode 15)

In the episode of Undercover Boss (US) titled "Sky Zone", Jeff Platt, CEO of Sky Zone, jumps into action as a referee for a children’s dodgeball game. As the youngest CEO in the show's history, the 29-year-old boss is tasked with hiding his in-depth knowledge of the company while working in community relations. This episode of Undercover Boss follows Jeff Platt as he gets an inside look at the daily operations of Sky Zone, the world's first indoor trampoline park.

Throughout the episode, Jeff discovers how much hard work goes into running a successful trampoline park. He meets with Sky Zone's employees, who are dedicated to providing an enjoyable experience for customers. From supervising the dodgeball game to organizing fund-raising events, Jeff's efforts to maintain the company's standards of quality and safety are commendable. Through it all, Jeff learns that the most important thing is to have a positive attitude and treat everyone with respect.

The episode was rated 7.72 from 29 votes.

Undercover Boss (US) - S5E10

#6 - Massage Heights (Season 5 - Episode 10)


In the episode of Undercover Boss (US) titled Massage Heights, COO Shane Evans is faced with the challenge of overcoming her own aversion to touching other people in order to complete her undercover mission. Shane has to find the strengths and weaknesses of Massage Heights by working undercover with their employees. As COO, Shane has to learn to step out of her comfort zone by getting a massage and providing services to customers.

This episode of Undercover Boss allows viewers to witness Shane's growth in overcoming her fear of physical contact. Despite her initial discomfort, Shane is committed to completing her mission and gaining a better understanding of the company. Through her journey, she learns more about the people who make up Massage Heights and how they are driven to provide the best service to their clients. Shane also discovers how her actions have an effect on the day-to-day operations of the business.

The episode was rated 7.78 from 32 votes.

Undercover Boss (US) - S5E11

#5 - Mohegan Sun Casino (Season 5 - Episode 11)

In the episode of Undercover Boss (US) titled Mohegan Sun Casino, Chairman Bruce "Two Dogs" Bozsum goes undercover as an employee of the Mohegan Sun Casino. This episode follows Bozsum as he works in various departments of the casino and interacts with the staff while maintaining his disguise. He gets to experience the daily operations of the casino first-hand, from the perspective of an employee, and learns about the challenges and rewards of the job.

This episode of Undercover Boss provides an interesting insight into the life of a casino employee. Bozsum is able to identify some of the problems and issues that the employees face on a daily basis, as well as the rewards and benefits of working at the casino. He also is able to appreciate the hard work that the employees put in to ensure that the casino runs smoothly. Overall, this episode provides an interesting look into the daily life of a casino employee and offers a unique perspective on the workings of the casino.

The episode was rated 7.81 from 42 votes.

Undercover Boss (US) - S5E4

#4 - Buffets, Inc. (Season 5 - Episode 4)


This episode of Undercover Boss follows the journey of Buffets, Inc. CEO Anthony Wedo as he goes undercover to learn more about the inner workings of his own company. During his time undercover, Wedo encountered an employee with a nasty attitude. Despite this, Wedo was still able to gain insights on how the company operated. Additionally, Wedo was able to learn how to work the grill station while undercover.

The mission of Undercover Boss is to let the CEO of a company experience the everyday operations of their own company in order to gain a better understanding of the organization. By doing so, it allows the CEO to get a better idea of how to improve the company. In this episode, Wedo was able to learn more about the inner workings of Buffets, Inc. and was able to gain insights that would have not been possible without going undercover.

The episode was rated 7.82 from 44 votes.

Undercover Boss (US) - S5E3

#3 - Donato's (Season 5 - Episode 3)

In the episode of Undercover Boss (US), Donato's, Jane Grote Abell, chairwoman of Donato's pizza, goes undercover to investigate the operations of one of her stores. She soon discovers that pizza isn't the only thing getting cooked up at this store. As she gets to know the employees and their stories, she realizes how hard they work and how passionate they are about their jobs and the company. She also discovers that the store is facing some challenges, such as long hours and a lack of resources.

Throughout the episode, Jane Grote Abell uses her undercover mission to find out what is going on in the store and to see how she can help. She discovers that the store needs an upgrade, that the employees could use more support, and that the store needs more resources to meet customer demands. She also discovers that the employees are underpaid, and she uses this knowledge to make changes to the store and to reward the employees with bonuses and more hours. At the end of the episode, she has made a lasting difference in the store and has given the employees a renewed sense of hope for the future.

The episode was rated 7.85 from 40 votes.

Undercover Boss (US) - S5E1

#2 - Twin Peaks (Season 5 - Episode 1)


In this episode of "Undercover Boss," CEO Randy Dewitt of Twin Peaks goes undercover at one of the sports bar and grill chain locations. Under the alias of 'Randy Ray', Dewitt is accompanied by Coby Brooks, an "Undercover Boss" alum and franchise owner at Twin Peaks. As Randy Ray, Dewitt is able to explore the restaurant, talk to the staff and customers, and observe the daily operations of the business.

During his undercover mission, Randy Dewitt is able to discover the difficulties the staff members face while running the restaurant. He also realizes the importance of customer service and the impact it has on the business. By the end of the episode, he is able to identify how he can improve the business and make changes that will benefit the staff, customers, and ultimately the company.

The episode was rated 7.85 from 47 votes.

Undercover Boss (US) - S5E9

#1 - Undercover Boss: Busted! (Season 5 - Episode 9)

Undercover Boss: Busted! takes a look back at previous episodes of the hit show Undercover Boss. Seven of the series' "Bosses" sit down to reflect on their experiences going undercover and the challenges they faced in keeping their true identity a secret. The bosses also provide updates on some of the memorable employees they encountered along the way.

This episode provides insight into the successes and failures of the undercover mission and it allows viewers to revisit the people and stories that have touched them in a powerful way. It's an opportunity to learn more about the show's impact on the lives of the bosses and their employees. The episode also serves as a reminder of how much a few simple acts of kindness can really make a difference in people's lives.

The episode was rated 8.08 from 26 votes.

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