Dean Martin
As the epitome of laid-back cool, the handsome, mellow-voiced crooner Dean Martin successfully redefined his image throughout his career without ever straying too far from his established persona as a quick-witted, booze-loving regular guy. Martin emerged from the shadow of playing straight man to his early comedy partner Jerry Lewis, to become a respected film actor in such films as "Some Came Running" (1958), as well as a top-selling solo recording artist. His profile rose even further as the apparent second-in-command to his close friend Frank Sinatra in the Rat Pack, both in films and on records and the stages of Las Vegas nightclubs. By the 1960s Martin was one of the most popular and highest paid performers in history, with a hit single that bounced the Beatles off the charts, films like the Matt Helm series topping the box office, and his long-running comedy-variety series, "The Dean Martin Show" (NBC, 1965-1974), sitting atop the ratings each week. Martin's output decreased somewhat in the 1970s and 1980s, but his appearances in films like "Airport" (1970) and "The Cannonball Run" (1981) continued to endear him to a broad audience. However, by the time of Martin's death in 1995, a resurgence of appreciation for Sinatra, Sammy Davis Jr., and their contemporaries - fueled perhaps most prominently by Jon Favreau's über-cool film "Swingers" (1996) - elevated the entertainer to full-fledged icon status. Though his former partner Jerry Lewis would later call him "the most underrated performer in the history of our business," Martin was enthusiastically embraced by the audiences of his time, and rediscovered by subsequent generations of fans who had yet to be born during his heyday.