Frank Sinatra Sr. was one of America's most beloved crooners and a legendary member of Hollywood's Rat Pack, the über-exclusive booze-soaked social club of the '60s whose wild and animated membership included Dean Martin, Sammy Davis Jr., and Joey Bishop.
Sinatra's son, Frank Jr., also rolls with one of Hollywood's most animated gangs, though literally of the cartoon variety. In 2006, Sinatra Jr. played himself on an episode of Seth MacFarlane's Family Guy. Together with the show's anthropomorphic dog, Brian, and sexually ambiguous baby, Stewie, Frankie and company tour the fictional town of Quahog in "Brian Sings and Swings." The gang channels its inner Rat Pack, womanizing and drinking like it's 1962 in Vegas. Then Brian hits rock bottom and it all ends hilariously.
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Sadly, Brian and Stewie don't travel with Sinatra Jr. in real life. But the 68-year-old's solo act is still a singing, swinging blast.