The Life and Times of Frank Sinatra: How a Legend Became His Own Worst Enemy

From Hollywood to Vegas

Sinatra tried to pursue an acting career in the early 1940s. And while films appealed to him, he was rarely enthusiastic about his acting, once saying that his “pictures stink.” His film debut was in an uncredited sequence in ‘Las Vegas Nights’ (1941), singing the song “I’ll Never Smile Again.” By the early 1950s, Sinatra’s professional career had stalled for a bit, and having felt rejected by Hollywood, he turned to Las Vegas.

FILM STILLS OF 1947, CHARITY, ED

Charity, Ed “Archie” Gardner, Danny Kaye, Frank Sinatra, Red Skelton in 1947. Photo By Snap/Shutterstock

It was in Vegas that he became one of the best-known residency performers as part of the Rat Pack. His debut was at the Desert Inn in 1951. He eventually became one of Las Vegas’s pioneer residency entertainers and a major figure on the strip throughout the 50s and 60s. The Rat Pack provided Sinatra with an outlet for expressive banter and wisecracks.