With which band did Frank Sinatra record his first number-one song 'I'll Never Smile Again'?

Frank Sinatra recorded his first number-one song, “I’ll Never Smile Again,” with the Tommy Dorsey Orchestra. Sinatra supplied the lead vocal, while the recording also featured the vocal group the Pied Pipers.

The song was written by Canadian songwriter Ruth Lowe in 1939 after the death of her husband. Tommy Dorsey recognized its potential and recorded it in 1940 with his orchestra. Sinatra had joined Dorsey’s band the previous year, after an earlier stint with the Harry James Orchestra, and the recording became a turning point in his career.

“I’ll Never Smile Again” topped Billboard’s first national Best Selling Retail Records chart in 1940 and remained at number one for 12 weeks. Because it was credited to Tommy Dorsey and His Orchestra, some listeners mistakenly identify it as a solo Sinatra hit or associate it with Harry James.

The success made Sinatra nationally prominent and helped launch the solo career that began when he left Dorsey’s orchestra in 1942. The recording is therefore important both as a Dorsey hit and as Sinatra’s first chart-topping breakthrough.