The Departed star is stopped whenever he lands on American soil and spends up to four hours sitting in a holding cell while authorities check his credentials.
The Hollywood hardman admitted he has convictions for assault but he's convinced it's his cannabis possession charge dating back to the mid-1970s that alerts officials.
Winstone tells London's Time Out magazine, "When I was a kid, my first acting job away was in Torquay (in England), and everyone had a party in my room... I can't smoke waccy baccy (cannabis), it sends me mad but everyone else was.
"The next day they spun (checked) my room over and found a bit. Rather than my dad finding out, I said, 'Yeah, I'm guilty'. Now I have to sit in a room in the airport in America for four hours every time I go."