Songfacts®:

• In this song, Frank Sinatra, one of the most famous entertainers of the 1940s and 1950s, represents that era - a time before the Rock Era when listening to his records was a common source of entertainment during this simpler time.
  
  "It sums up a lot of the misunderstandings between the generations," Cake trumpet player Vince DiFiore told the Arizona Wildcat. "Since Frank Sinatra is a part of the previous generation, he illustrates that gap."
• "Frank Sinatra" is an early Cake song, part of their second album, Fashion Nugget, released in 1996. It was released as the third single from the album, following their breakout hit "The Distance" and their laconic cover of the disco favorite "I Will Survive."
• A faintly glimmering radio station
  While Frank Sinatra sings "Stormy Weather"
  
  "Stormy Weather" is a standard written in 1933 and popularized by Lena Horne in 1943. Frank Sinatra covered it in 1945.
• The members of Cake are Frank Sinatra fans and see this song as tribute. "I think a lot of people overlook what a genius he was in terms of phrasing and interpretation of melody," John McCrea said (as quoted in the Asbury Park Press). "If you listen to the way he phrases a song, I don't think there's anybody better at timing and phrasing and accentuation of lyrics and melodies."
• "Frank Sinatra" was never a hit but is a favorite among the band and their fans. Cake usually include it in their setlists.
• Note how in the first verse lead singer John McCrea's voice is processed to sound like it's coming from an old speaker of the kind Frank Sinatra records were played on in days of yore. In the second verse he gets his full dynamic range, bringing us into modern times. Cake used similar vocal processing on their 1998 hit "Never There," but that one simulates a phone line.
• The song plays at the end of the season 1 episode of The Sopranos, "The Legend of Tennessee Moltisanti." Sinatra was from New Jersey, where the show was set.