(Sittin' On) The Dock of the Bay — Otis Redding (1968)

Otis Redding's '(Sittin' On) The Dock of the Bay' became the first posthumous #1 on the Billboard Hot 100 in 1968, spending 4 weeks at the top and selling over 4 million copies. Written on a Sausalito houseboat in October 1967, three months before his fatal plane crash, Redding's whistled outro—improvised to fill an unfinished ending—remains one of music's most recognized sounds. The song's 4-week Hot 100 reign is 2 weeks shorter than #1 Aretha Franklin's 'Respect' (2 weeks at #1 on Hot 100), but its Grammy-nominated legacy and 1.5 million streaming plays daily in 2024 surpass the typical posthumous hit's longevity.