Conversation so far:
Why did Frank Sinatra have a career slump?
Both of Sinatra's films Double Dynamite (1951), an RKO Irving Cummings comedy produced by Howard Hughes, and Joseph Pevney's Meet Danny Wilson (1952) failed to make an impression
What was Frank Sinatra's debut film?
Sinatra made his film debut performing in an uncredited sequence in Las Vegas Nights (1941), singing I'll Never Smile Again with Tommy Dorsey's Pied Pipers
Who was in the film Las Vegas Nights with Frank Sinatra?
Sinatra made his film debut performing in Las Vegas Nights (1941) with Tommy Dorsey's Pied Pipers
Was Las Vegas Nights a musical film?
Yes, Sinatra sang I'll Never Smile Again with Tommy Dorsey's Pied Pipers
Did Frank Sinatra have other musical films besides Las Vegas Nights?
He had a cameo role along with Duke Ellington and Count Basie in Charles Barton's Reveille with Beverly (1943), making a brief appearance singing Night and Day“
Did anything interesting happen to Frank Sinatra during 1941-1952?
Frank Sinatra was in a series of films from 1941-1952, including Las Vegas Nights, Higher and Higher, Anchors Aweigh, and Till The Clouds Roll By
Did Frank Sinatra star in any other movies besides Las Vegas Nights, Higher and Higher, Anchors Aweigh, and Till The Clouds Roll By after 1949?
Yes; Frank Sinatra starred in Take Me Out to the Ball Game (1949), On the Town (1949), Double Dynamite (1951), and Meet Danny Wilson (1952)
Did Frank Sinatra sing in the movies Take Me Out to the Ball Game (1949), On the Town (1949), Double Dynamite (1951), or Meet Danny Wilson (1952)?
Yes; Frank Sinatra and Gene Kelly sang in On the Town (1949), which in 2006 ranked number 19 on the American Film Institute's list of best musicals

Question: did he stay friends with Irving Cummings?
Self-contained rewrite: Did Frank Sinatra stay friends with Irving Cummings?