Never dealt with the weed thing, but a friend of mine has a DUI on his record, and it is hit or miss whether they let him across the border apparently.
I went with him to a Red Wings game before and the border agent was nice but made the point that he could be denied entry, but they would let him through that one time. The American border agent also said that if it was the opposite, Canada almost never makes exceptions and any American with a DUI would be denied entry into Canada. Not sure if that is true or if he was exaggerating.
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