The WORST episodes of Undercover Boss (US)

Every episode of Undercover Boss (US) ever, ranked from worst to best by thousands of votes from fans of the show. The worst episodes of Undercover Boss (US)!

In this hidden camera show, high-level corporate execs leave the comfort of their offices and secretly take low-level jobs within their companies to find out how things really work and what their employees truly think of them. In the process of this undercover mission, they learn of the perceptions about their companies, the spirit of their work forces and maybe, something about themselves as well. Based on the UK series of the same name.

Last Updated: 9/16/2025Network: CBSStatus: Ended
Bikinis Sports Bar & Grill
star
6.21
70 votes

#1 - Bikinis Sports Bar & Grill

Season 6 - Episode 3 - Aired 12/28/2014

CEO/Founder Doug Guller of Bikinis Sports Bar & Grill, who welcomes controversy and proudly refers to his chain of restaurants as "breastaurants". While undercover, Guller contends with a troublesome employee who not only refuses to don the uniform’s bikini top, but also over-serves an intoxicated person.

Watch Now:Apple TV
1-800-Flowers
star
6.40
117 votes

#2 - 1-800-Flowers

Season 1 - Episode 9 - Aired 4/11/2010

Chris McCann, President and COO of 1-800-FLOWERS, America's largest florist and online gift shop, goes undercover and is later forced to reveal his true identity on the season finale of Undercover Boss.

Watch Now:Apple TV
Peavey Electronics
star
6.63
48 votes

#3 - Peavey Electronics

Season 6 - Episode 12 - Aired 2/15/2015

Courtland Gray, COO of Peavey Electronics, goes undercover to see what keeps his audio empire rocking, Also, the company makes a shocking announcement after filming the episode that changes two employees' lives.

Watch Now:Apple TV
White Castle
star
6.67
153 votes

#4 - White Castle

Season 1 - Episode 4 - Aired 2/28/2010

While under cover in the company, White Castle owner Dave Rife mishandles bakery equipment.

Watch Now:Apple TV
Maaco
star
6.71
65 votes

#5 - Maaco

Season 6 - Episode 4 - Aired 1/2/2015

Jose Costa, the Venezuelan-born President of Maaco, goes under the hood to inspect "America's Bodyshop". On the job, the boss gets overheated when he finds an employee cutting corners. Additionally, the boss’s detailing work could stand to be fine-tuned.

Watch Now:Apple TV
Armando Montelongo
star
6.75
28 votes

#6 - Armando Montelongo

Season 6 - Episode 10 - Aired 2/6/2015

Armando Montelongo, CEO of Armando Montelongo Companies, a top real estate company that specializes in educational seminars that teach wealth creation and financial independence, goes undercover to see what keeps his real estate investment company on solid ground. For the first time in UNDERCOVER BOSS history, Montelongo hires a body double to help conceal his identity while undercover at one of his seminars.

Watch Now:Apple TV
United Van Lines
star
6.79
77 votes

#7 - United Van Lines

Season 2 - Episode 17 - Aired 3/13/2011

Rich McClure, the CEO of United Van Lines, the nation's largest moving company, asks his wife to assist him during one of his undercover jobs. Meanwhile, the boss' moving team fears he won't make it through the physically demanding task of wrapping, packing and loading an entire move.

star
6.89
92 votes

#8 - Undercover Employee

Season 5 - Episode 14 - Aired 3/7/2014

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.

Watch Now:Apple TV
star
6.89
145 votes

#9 - MGM Grand

Season 2 - Episode 18 - Aired 3/20/2011

Scott Sibella, President and COO of the MGM Grand in Las Vegas, goes undercover within the walls of the second-largest hotel in the world and faces a group of rowdy gamblers who are quick to point out his shortcomings as a dealer. Meanwhile, the boss also becomes frustrated with the slowness of their computer system while attempting to check-in guests.

star
6.91
132 votes

#10 - Synagro

Season 2 - Episode 19 - Aired 3/27/2011

Bill Massa, the President and CEO of Synagro, the largest wastewater treatment company in America, goes undercover posing as a former employee of a company that damaged the environment training with environmentally friendly companies.

Mayor of Pittsburgh
star
6.92
61 votes

#11 - Mayor of Pittsburgh

Season 6 - Episode 2 - Aired 12/21/2014

The Mayor of Pittsburgh, Bill Peduto, does a stint as a municipal employee in the Steel City. During his shifts, Peduto performs jobs as a refuse worker, a carpenter, a self-sufficiency coordinator and a Public Works employee who cuts down dead trees.

Watch Now:Apple TV
star
6.95
44 votes

#12 - City of Cincinnati

Season 2 - Episode 16 - Aired 3/6/2011

The mayor of Cincinnati, Mark Mallory, becomes the first elected official to go undercover as he trades in his key to the city for a stint as a municipal employee, working as a mechanic repairing public transportation vehicles and a sanitation worker whose job entails removing roadkill from the streets.

star
6.98
81 votes

#13 - Kendall-Jackson Wine Estates

Season 3 - Episode 3 - Aired 1/29/2012

Rick Tigner, President of Kendall-Jackson Wine Estates goes undercover in his Luxury wine company.

star
6.98
52 votes

#14 - Celebrity Undercover Boss: Bethany Mota

Season 9 - Episode 3 - Aired 5/25/2018

YouTube sensation Bethany Mota channels a punk rocker when she goes undercover to link up with and mentor potential YouTube stars. While pretending she wants to start her own YouTube channel, Mota hopes things will click when tasked with teaching a dance class for a YouTube channel; picks up the beat in a beatboxing challenge on Hollywood Boulevard; and fears she won't be able to keep it together when faced with eating a cricket during a YouTube food challenge.

Watch Now:Apple TV
Phenix Salon INC.
star
7.05
56 votes

#15 - Phenix Salon INC.

Season 6 - Episode 5 - Aired 1/9/2015

Gina Rivera, Founder and President of Phenix Salons INC., a franchise which offers independent salon and business professionals the opportunity to own and operate their own luxury salon suites, goes undercover to see if it will color her perception of how the company is running,

Watch Now:Apple TV
Bowlero
star
7.07
30 votes

#16 - Bowlero

Season 10 - Episode 6 - Aired 10/9/2020

Colie Edison, chief customer officer of Bowlero Corp and CEO of the Professional Bowlers Association, works to spare the customers from waiting too long when checking them in to bowl, and tries for a perfect game while taking food orders as a lane server.

GSI Commerce
star
7.07
119 votes

#17 - GSI Commerce

Season 1 - Episode 6 - Aired 3/21/2010

Michael G. Rubin, Chairman, President and CEO of GSI Commerce, the e-commerce giant behind numerous top U.S. retailers, goes undercover in his own company, where he discovers that rushing through a task can result in injury to others, and that his packing and shipping skills are not up to company standards.

Watch Now:Apple TV
Roto-Rooter
star
7.07
115 votes

#18 - Roto-Rooter

Season 1 - Episode 8 - Aired 4/4/2010

The president of Roto-Rooter works under cover with several employees who force him to reflect on his past and his legacy.

star
7.07
68 votes

#19 - Dutch Bros. Coffee

Season 5 - Episode 8 - Aired 11/15/2013

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

Watch Now:Apple TV
Subway
star
7.11
123 votes

#20 - Subway

Season 2 - Episode 9 - Aired 11/21/2010

Don Fertman, the Chief Development Officer for SUBWAY restaurants, one of the world's largest food franchises, goes undercover where he learns endless sandwich combinations while being trained by one of the toughest, no-nonsense employees ever

star
7.11
64 votes

#21 - Tilted Kilt

Season 4 - Episode 2 - Aired 11/9/2012

Tilted Kilt President Ron Lynch goes under cover.

Watch Now:Apple TV
Modell's Sporting Goods
star
7.14
87 votes

#22 - Modell's Sporting Goods

Season 4 - Episode 1 - Aired 11/2/2012

Modell's Sporting Goods CEO Mitchell B. Modell goes under cover.

Watch Now:Apple TV
star
7.14
58 votes

#23 - PostNet

Season 4 - Episode 5 - Aired 12/7/2012

When PostNet CEO Steve Greenbaum goes under cover, he meets a veteran adjusting to civilian life and encounters struggling franchise owners.

Watch Now:Apple TV
Celebrity Undercover Boss: Deion Sanders
star
7.14
43 votes

#24 - Celebrity Undercover Boss: Deion Sanders

Season 9 - Episode 4 - Aired 6/1/2018

Two-time Super Bowl champion and Pro Football Hall of Famer Deion Sanders tackles an undercover mission to reward youth football coaches and give back to his community.

Watch Now:Apple TV
Churchill Downs
star
7.15
127 votes

#25 - Churchill Downs

Season 1 - Episode 5 - Aired 3/14/2010

Bill Carstanjen, President & COO of Churchill Downs, goes undercover at his own racetracks. This however proves difficult as he is afraid of horses.

Watch Now:Apple TV