44 entries

Every Frank Sinatra recording to have appeared on the Billboard Hot 100 singles chart, per Billboard's official artist chart-history page (billboard.com/artist/frank-sinatra/chart-history/hsi/): 44 charting titles in all, including 2 No. 1 hits (“Strangers In The Night” and “Somethin’ Stupid,” the latter a duet with Nancy Sinatra) and 3 Top 10 hits. Unlike Billboard’s own page, which orders entries by peak chart position, this appendix lists them in true chronological order by chart-debut date, oldest to newest, so the list can be read alongside the main STAOST chronology. For each title: the recording artist credit as shown by Billboard, chart-debut date, peak position reached and the date it was reached, and total weeks on the chart.

A note on “Jingle Bells”: its listed dates (debut January 2019, peak December 2023) are not a transcription error. The 1957 Sinatra/Gordon Jenkins recording re-entered the Hot 100 during the 2019 and 2023 holiday seasons under Billboard’s modern streaming- and airplay-inclusive chart methodology for recurring holiday songs -- it did not chart in its original release year. It is placed accordingly, near the end of this chronological list rather than in the 1950s.