Christy first appeared on The Howard Stern Show in October 1999, where Stern would play voice mail messages that Christy had recorded about co-host Robin Quivers. His debut message was featured on the Labor Day Weekend special in 2006. Christy would continue sending in messages but it was not until April 24, 2003, when the show would broadcast from the Hard Rock Hotel and Casino in Las Vegas, where Christy made his debut appearance. Christy unsuccessfully played a round of blackjack to win a date with a porn star.
In 2004, John Melendez (then known as "Stuttering John") left the radio show to become the announcer for The Tonight Show with Jay Leno. Stern announced a "Get John's Job" contest which pitted ten Stern fans and contributors against each other in competition for Melendez's vacated position. Each contestant was given a week to display any talents they could bring to the show, after which the listeners cast votes for their favorite over the Internet. On July 1, Stern announced Christy had won with 30% of the listener vote, with Sal Governale being runner-up with 24%; both Christy and Governale joined the show by September.
When Stern moved to Sirius XM Radio in January 2006, he gave Christy his own show that would air semi-regularly throughout the year. On May 15, 2006, porn star Hillary Scott was the first guest on Inside the Porn Actors Studio on Howard 101, an hour-long program which parodied the television series Inside the Actors Studio, with Christy filling the role of James Lipton.
Between 2005 and the tour's demise in late 2009, Christy also performed in The Killers of Comedy Tour with fellow Stern castmembers across the United States and Canada.
In 2006, Christy hosted a program on Sirius XM channel Hard Attack called "Richard Christy's Heavy Metal Hoedown".
After the 2009 Thanksgiving holiday, Christy returned to the show suffering from swelling and severe pain in his foot. It was later diagnosed as gout, which is extremely rare in someone as young as Christy. The pain and swelling quickly receded after treatment, and he announced on December 17, 2009 that because of his fame and his frank on-air discussions about the disease, a gout awareness organization had requested that he become a spokesperson for the disease, and he had agreed.
On the December 17, 2009 Howard Stern Show, Christy announced that not only had he showered the previous day, but that he also became engaged to his longtime girlfriend, known on the show only as "Kristen the Intern".
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