There has been people wondering if Michael Jackson and Charlie Chaplin ever met. They did not. Michael was a famous child and teenage singing star with the Jackson 5, as well as some solo work during Chaplin's later years. Michael was a huge fan of Chaplin's and the song 'Smile' was his favorite song. Jackson did say he always wanted to meet Oona Chaplin, which he did in the 1980s.
According to Jane Scovell book - 'Oona: Living in the Shadows'
"Oona's old friend Sophia Loren, "something of a Jackson groupie," had been attending Jackson's concerts, and when the singer came to Switzerland the Italian actress did arrange for them to meet. He (Michael Jackson) went to the Manoir and was given a tour of the estate by Oona. At one point she told him that he and Charlie "had a lot in common: you were born poor and had to strive to achieve all that you have." - 'Oona: Living in the Shadows' by Jane Scovell
Chaplin's home? Here is a tour of the Manior in Switzerland by Chaplin fan Rainer Mann. LINK
Update: Aug. 24th - Link to a painting Michael did of Chaplin when he was nine years old.
Update: Dec. 9, 2009 - LA Times Magazine, Michael Jackson dressed as Chaplin.
Update: Dec. 9, 2009 - More about Michael Jackson as Charlie Chaplin photo shoot.
Update Mar. 24, 2010 - 'Charlie and Michael' impersonators at the Adamastor Theatre.