Lots of semi-famous musicians/groups (I was a roady for a few years) like the members of Hydra, Blue Oyster Cult, Triumph etc. A couple famous ones- Ted Nugent and Todd Rundgren at different times.
Tex Cobb for a night of drunkeness on his tab (He had just won a tax case in Tennesee) Tex was the motorcycle bounty hunter guy in Raising Arizona.
Carrot Top. He just happened to be staying at the same hotel as I and I bought him a drink in the hotel bar. He reciprocated.
Many sports types. I lived a block from William Perry during the Bears Super Bowl year. I worked as Host at a restaraunt that was popular with a few of the Bears and Bulls. Met Walter Payton when he came to ride horses at my girlfriend's house.
Jim Edgar - former Governor of Illinois, had lunch just recently in my fav spot.
Cardinal Joseph Bernadin - I worked at St. Mary of the Lake Seminary (where his retreat was) Center for Development in Ministry. Mixed many a drink (he liked Manhattans) for him and other priests during social gatherings after conferences.
I know I'm forgetting some.