Wilkinson danced at Cheetah's Strip Club in San Diego, CA, before Wilkinson met Hefner at his 78th birthday party in April 2004, where she had been hired to be one of the "painted girls": women who are completely nude except for painted-on accessories. Apparently he had seen her picture on a fax machine at the Playboy Mansion and wanted to know who she was. Shortly after they met, Hefner asked Kendra to be one of his girlfriends and he moved her into the
Playboy Mansion.
Wilkinson has made several cameos on different programs such as
Las Vegas,
Entourage and
Curb Your Enthusiasm. She also appeared in
Akon's music video "
Smack That." While on the set of the video,
Eminem poured a bottle of water on her head, sparking an altercation. The incident was discussed on
The Girls Next Door.
Kendra also showed her creative side as a rapper on MTV's
Celebrity Rap Superstar which debuted on August 30, 2007. Wilkinson rapped to
Ludacris’ “Fantasy”, apparently in response to the question asked by the show's host, “Can Kendra move her mouth as fast as she moves her booty?” She went on to take second place, losing to
Shar Jackson on October 18, 2007.
Her stated career goal is to become a massage therapist or sports announcer. As of December 2005, she has become a regular "blogger" columnist at the website of the
Philadelphia Eagles, the team for which her mother had been a professional cheerleader.
Wilkinson is coming out with her own clothing line, Kdub Clothing.
Kendra owns two dogs, a Pembroke Welsh Corgi named Rascal and a Jack Russell Terrier named Martini, as seen on
The Girls Next Door. In 2007, she appeared in Nickleback's music video of "
Rockstar", along with Girls Next Door co-stars,
Holly Madison and
Bridget Marquardt