Stand-up career According to Bailey, he was telling stories with some comedians after hours at
The Comedy Store (where he worked as a bartender and bouncer) when
Skip E. Lowe, who was
emceeing at the club, found his stories humorous and offered him an opportunity to perform
stand-up. Bailey soon returned to the East Coast, where he gained popularity at comedy clubs in New York City. He has since performed at major festivals such as
Just For Laughs and the
Edinburgh Fringe Festival. As of 2019, he toured as a headliner. During the
COVID-19 lockdowns, Bailey streamed his comedy show
Work from Home to YouTube, with his girlfriend as co-host and producer. He filmed the show in his basement. In 2006, he starred in his first special on
Comedy Central,
Comedy Central Presents Ben Bailey. In 2011, he released a two-part special,
Road Rage and
Accidental Ornithology. In 2016, he released
Ben Bailey Live & Uncensored and in 2024, he released the
Please Tell Me What I Said special on his YouTube channel.
Cash Cab and other endeavors Bailey was the host and producer of the American version of
Cash Cab, a TV game show played in a
taxicab that Bailey drives around
New York City, broadcast on the
Discovery Channel and
Bravo. He hosted the show for all of its 14 seasons, including its initial run from 2005 to 2012, as well as its return from 2017 to 2020. He also hosted the short-lived 2007 spin off
Cash Cab After Dark. Bailey also appeared on the new Shovio.com's
TalkBackTV. He narrated the
Discovery Channel's series
Smash Lab. From 2011 to 2012, he was the host of ''
Who's Still Standing?'' on NBC; the show was not renewed for a second season due to high production costs. He has also appeared in
ABC's
The Knights of Prosperity,
Hope & Faith,
NBC's
Law and Order SVU, and Fox's
Mad TV, and has also appeared in
Blue Bloods,
30 Rock, with a recurring role on
One Life to Live. He has appeared on talk shows such as
The Tonight Show,
The Today Show,
Oprah,
Rachel Ray,
Good Day New York, and numerous morning/radio shows nationwide. He has done television commercials for
ALDI and Michigan electric/natural gas company
DTE Energy . From 2022 to 2023 Bailey hosted
Money Grab in the Cab, a show very similar to
Cash Cab, in which he drove around giving farmers 10 minutes to answer as many questions as they could in order to earn money for their local
FFA chapter. In 2023 Bailey appeared in
The Game Show Show, a documentary about the history of game shows. In 2025 Bailey partnered with the
Kansas City Chiefs to create a video special titled "The Chiefs Cab" which was inspired by
Cash Cab. In the special Bailey drives around members of the Chiefs organization and asks them questions. ==Personal life==