There was two significant times I remember Duluth being featured on the Tonight Show with Jay Leno. One was about a movie poster and the other involved Club Saratoga. 

Back when Jay Leno hosted the Tonight Show he would always do a segment called 'Headlines' which highlighted humorous headlines in newspapers across the country.

The first time Duluth was mentioned to my knowledge was when the movie 'White Palace' was released. The poster was a little racy and each week the paper tried to cover up the racy image.

The second time was when Club Saratoga located in Canal Park were looking for pole dancers. Apparently people were confused by their slogan: 'Always A Polished Stage'.

These two memories definitely gave me a good laugh. Let me know when in the comments if you remember other times Duluth was mentioned on late night talk shows.