Frank Sinatra was one of America's most beloved crooners and a legendary member of Hollywood's "Rat Pack" — the über-exclusive cigarette-smoke- and booze-filled social crew of the 1960s, made up of a rather animated bunch: Frankie, Dean Martin, Sammy Davis Jr., and Joey Bishop. Sinatra's son, Frank Jr., on the other hand, may roll with one of Hollywood's most animated groups these days; however, they're of a cartoon variety. In 2006, Sinatra Jr. appeared on an episode of Seth MacFarlane's Family Guy as an animated version of himself. Together with the show's anthropomorphic dog, Brian, and sexually ambiguous baby, Stewie, Sinatra Jr. and company tour the fictional town of Quahog in "Brian Sings and Swings." The group channels its inner Rat Pack, womanizing and drinking heavily throughout the episode like it's Las Vegas in 1962. Sadly, Brian and Stewie don't travel with Sinatra Jr. in real life, but the 68-year-old's solo act is nevertheless entertaining for a more mature crowd that appreciates quality music over perverted jokes.