Being hung up on the '60s, there is and will be only one clown for me, Bozo the Clown. After Bozo I had no truck with clowns. I'm a serious man. But I can relate to this segment from the Seinfeld episode, "The Fire." It is one of the funniest in the whole series. But I suppose you had to be there. In the '60s I mean. With Bozo. The Clown. Now some songs featuring clowns.
Roy Orbison, In Dreams. "A candy-colored clown they call the sandman . . . ."
James Darren, Goodbye Cruel World. "I'm off to join the circus, gonna be a broken-hearted clown."
Frank Sinatra, Send in the Clowns
Everly Bros., Cathy's Clown
Burl Ives, A Little Bitty Tear. A little bitty tear let me down, spoiled my act as a clown/ I had it made up not make a frown, but a little bitty tear let me down.
Smokey Robinson and the Miracles, The Tears of a Clown
Kinks, Death of a Clown
Harry Nilsson, 1941