Sir Paul McCarnety
#1: The Scaffold - Lily The Pink
https://www.youtube.com/watch?v=u7pHDoJrrzA

(Backing vocalists on the recording included Graham Nash (of the Hollies), Elton John (then Reg Dwight), and Tim Rice; while Jack Bruce (of Cream) played the bass guitar.)

#2: The Scaffold - Liverpool Lou (with special guests Paul McCartney and Wings.)
https://www.youtube.com/watch?v=MjnkmNyArNg

Why? His brother is in the band. (Mike McGear.) According to wikipedia the song hit #1 on the charts on Christmas Day in 1968. #2 is suggested if you want even a song they both performed on.



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Tony Bennett & Lady Gaga
Let's Duet - Dewey and Darlene Madison Cox
https://www.youtube.com/watch?v=UP5YFr4SkCQ






EDIT: Questions:
1)Did this show already tape?
2) Fuck North Korea!