Kendra met Hugh Hefner at his 78th birthday party in April 2004, where she was hired to be one of the « painted girls » (women who are nude except for painted-on accessories).

Hefner had apparently seen her picture, shot by photographer Kim Riley, on a fax machine at the Playboy Mansion and wanted to know who she was. Shortly after they met, Hefner asked Wilkinson to be one of his girlfriends, and he moved her into the Playboy Mansion along with her dogs Rascal (a Pembroke Welsh Corgi) and Martini (a Jack Russell Terrier).

She was featured on the E! reality television series The Girls Next Door, which followed the lives of Hefner’s then-girlfriends: Wilkinson, Holly Madison, and Bridget Marquardt. She moved out of the Playboy Mansion in 2009 after meeting her future husband,Hank Baskett, and filmed her own spin-off reality show for E! called Kendra. The first season was about her living on her own and planning her wedding.

Wilkinson has made several cameos on different programs such as Las Vegas and Entourage. 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, though the two later reconciled. In 2006, she appeared in the Playboy Special Editions Sexy 100. In 2007, she appeared in Nickelback’s music video of « Rockstar », along with Madison and Marquardt. They also had a cameo role in the 2006 film Scary Movie 4. Wilkinson also showed her creative side as a rapper on MTV’s Celebrity Rap Superstar which debuted on August 30, 2007. She rapped to Ludacris’ « Fantasy », 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.

Wilkinson’s stated career goal is to become a massage therapist or sports announcer. In December 2005, she became a regular blogger columnist at the website of the Philadelphia Eagles, a team for which her mother had been a professional cheerleader,[16] and for which her husband played professionally.

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