"I'll Never Smile Again" is a popular song written by Ruth Lowe in 1939 and recorded and made famous by Tommy Dorsey and His Orchestra, with Frank Sinatra providing the vocal. It was the first ever #1 hit on the Billboard weekly Best Selling Singles chart by Tommy Dorsey and His Orchestra as Victor 26628 in 1940.

The best known version of the song is the 1940 recording by the Tommy Dorsey Orchestra featuring Frank Sinatra (Victor 26628). This version stayed at no.1 for 12 weeks, from July 27 to October 12, 1940, and was inducted into the Grammy Hall of Fame in 1982. Tommy Dorsey also recorded the song on V-Disc, V-Disc 582, also with Frank Sinatra on vocals. Glenn Miller and His Orchestra also recorded a version of the song in 1940.

In 1965, Sinatra re-recorded the song for the double album A Man and His Music, complete with faithful reproduction of the tinkling celeste and choral accompaniment which characterized the 1940 recording.

It has been recorded by many other artists since, becoming a standard. The Platters brought the song back to the top 40 in 1961.