220px-Joe_Cocker-With_a_Little_Help_from_My_Friends_(album_cover)#10– Joe Cocker – “With A Little Help From My Friends” – (1969)

It takes some serious balls to cover The Beatles (Sgt. Pepper-era Beatles at that) and think you can better one of their tracks. But that’s just what Joe Cocker did. It’s one of the best covers of all time and that’s partly because he dissected the song, and rebuilt it to suit his style, bringing in other musicians to help re-arrange it. It’s brilliant – and so was his performance of it at Woodstock which became quite famous on its own.

220px-I_Can_Stand_a_Little_Rain#15 – Joe Cocker – “You Are So Beautiful” – (1974)

Co-written by Billy Preston, this song was a big hit for Joe Cocker (even though he didn’t write it). It peaked at #5 on the Hot 100. There’s just something great about a love song sung by someone with such a gruff voice, especially when backed with such a nice, soft piano.

#68 – Bill Medley & Jennifer Warnes – “I’ve had the Time of My Life” – (1987)

Dirty Dancing was a landmark of the 1980s – both as a film and a soundtrack. The original soundtrack contained 12 tracks, about 9 of which were massive hits at one time or another. Three of those were first released on this soundtrack – which is quite a feat (one of which is featured elsewhere on this list). The other one was “She’s like the Wind” which was a #3 hit for Patrick Swayze. “I’ve had the Time of My Life” was performed by Righteous Brother Bill Medley and Queen of 1980s Film Theme Duets Jennifer Warnes (see also: “Up Where We Belong” with Joe Cocker, from 1982’s An Officer and a Gentleman). This song won an Oscar for Best Original Song and a Grammy for Best Pop Performance (Duo or Group) and it went to #1 on the Hot 100.