Tony Bennett photo courtesy Sony Music Archives/Don Hunstein

It took a lot of ill-fated singles before some ’50s pop stars got hits

While some lucky pop artists scored hits with their very first singles, others — including some outright legends — needed to try and try again before they finally broke through on Billboard Pop Charts. (Connie Francis famously put out 10 singles on MGM before she found success with 1958’s “Who’s Sorry Now?”) Here’s a peek at some other now-famous artists who needed at least two attempts to score chart hits back in the ’50s.

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