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As usual with Ace, the caption at the bottom of the painting tells the story.
It's hard to read on the webpage, so here's what it says:

" Sometimes in the middle of his busy day, Barak pauses and remembers his first date with Michelle when he took her to American Bandstand. To impress her, he jumped the velvet rope, grabbed a loose guitar and taught Chuck Berry to do the "duc wok", which he learned as a boy in Indonesia. The rest is cultural history. Michelle, of course, was absolutly his from that moment on."
Here are some details from "AMERICAN BANDSTAND" by Johnny Ace
THE CAST

Barack & Michelle Obama
Dick Clark
Chuck Berry
Pat Boone
Bo Diddly
The Everly Brothers
Little Richard
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