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He was hired away by WTJS for double the salary by Jackson's only other station, WDXI. He next hosted mornings at WHBQ in Memphis while a college student at Memphis State University, graduating with a Bachelor of Science degree in 1957. While there Martindale became a member of the Kappa Sigma Fraternity.
Martindale's rendition of the spoken-word song "Deck of Cards" went to No. 7 on the Billboard Hot 100 chart and sold over a million copies in 1959. It also peaked at No. 5 in the UK Singles Chart in April 1963, one of four visits to that chart. It was followed by "Black Land Farmer". In 1959, he became morning man at KHJ in Los Angeles, California, moving a year later to the morning show at KRLA and finally to KFWB in 1962. He also had lengthy stays at KGIL, KKGO/KJQI and Gene Autry's KMPC. In 1967, Martindale narrated a futuristic documentary which predicted Internet commerce.
Martindale hosted numerous game shows, including Gambit, High Rollers, Debt, and Tic-Tac-Dough, among others. In addition, Martindale also created the USA Network original game show Bumper Stumpers. Martindale is second in the most number of game shows hosted at 15, behind fellow veteran game show host, Bill Cullen, who hosted 23 shows.
On June 2, 2006, Martindale received a star on the Hollywood Walk of Fame. In 2007, Martindale became a member of the nominating committee of the Hit Parade Hall of Fame. On October 13, 2007, Martindale was one of the first inductees into the American TV Game Show Hall of Fame in Las Vegas, Nevada.
Martindale appeared in various TV commercials and was also the spokesman for Orbitz. Until 2007, Martindale had a daily three-hour show on the syndicated Music Of Your Life format, which is heard on around 200 radio stations. On June 2, 2009, Martindale signed with the syndicated Hit Parade Radio format. The format began operation on February 7, 2010, with Martindale as afternoon drive personality. The syndicator stopped operating on June 6, 2010.
In 2008, Wink appeared on GSN Live, an interstitial program during the afternoon block of classic game show reruns. Several times during 2008, Martindale filled in for Fred Roggin on GSN Live while Roggin was on vacation. Martindale's last show was the GSN show Instant Recall, which premiered on March 4, 2010. Instant Recall would be the first show Martindale has hosted since Debt aired on Lifetime from 1996 to 1998.