Answer:  4 times

#1 for one week in 1960 by Chubby Checker


#28 in 1960 for Hank Ballard & the Midnighters

#1 for two weeks in 1962, AGAIN! by Chubby Checker.  (This is the only song ever to come back and hit #1 in the Rock Era.)

And finally, a #16 hit for The Fat Boys and Chubby Checker in 1988 !

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