You Can Call Me Al by Paul Simon
A 60's icon gets a 70's comedian to help him make an 80's song fun.
Released in September of 1986, this was the lead single from his Grammy winning album, Graceland. This song reached the top 5 in seven different countries....but not in the US where it only reached #23. Paul probably didn't get too upset, the album went on to sell nearly 15 million copies and is listed on most "Top Albums of all time" lists.
The song was inspired by an actual moment where Paul and his wife went to a party and someone kept referring to him as Al and his wife as Betty (her name was Peggy). Inspiration comes where ever it comes.
The music video was produced after the original live performance video proved to be not very exciting. Paul was hosting Saturday Night Live and it was suggested that doing something silly would be better. Paul asked his friend (and SNL alum) Chevy Chase to help him out and he came through for him. The idea of Paul Simon singing back up vocals to Chevy Chase on his own song is immediately silly and when you add in the usual silliness that someone like Chevy can come up with in subtle humor (dropping a glass of water and a tin whistle through what is obviously NOT a side table being just a small example), well the video is a classic.
Sometimes the silliest idea is the best idea.