A caricature by John Lennon of the singer and his wife, Yoko Ono, drawn during their 1969 "bed-in" in Montreal, Canada, has sold for £37,250.
The piece, part of a rock and pop sale at Christie's in London, was created during their peace protest at the Queen Elizabeth Hotel.
A jacket worn by Michael Jackson also fetched £22,500 on the eve of the first anniversary of his death.
A guitar used by Pete Townshend, of The Who, fetched a top price of £49,250.
The Gibson SG guitar - part of the largest collection of Who memorabilia ever auctioned - was used on The Who's 1971 tour.
The Who collection, brought to auction by US collectors Brad and Diana Rodgers, went for a total of £169,946.
Mr Rodgers said he was "incredibly pleased" with his haul.
"This sale demonstrates that the market for high end, one-of-a-kind material, is as strong as it has ever been," he said.
Jackson's black sequined stage jacket had a pre-sale estimate of just £2,000.
Meanwhile, a Les Paul guitar smashed by Steve Jones, of the Sex Pistols, at a gig at London's 100 Club, sold for £16,250.