My Way without a doubt did more damage to Sinatra's career than good. People think they know him because of that one song. The majority of people would never give his great albums like 'Watertown', 'She Shot Me Down', 'Sings For Only The Lonely', and 'In The Wee Small Hours' even a chance because they think they know him through that one signature song that he didn't even like or connect with on a personal level. Sinatra himself said he thought it was an 'arrogant' song. If Sinatra thought it was arrogant...well....
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