Yesterday I promised to tell you the story behind this hat (and why I am making that face).
My first job out of college, I worked in public relations for Marshall Field's in Chicago. There is nothing quite like doing retail PR to give you a taste of everything that is out there. Fashion, finance, food and wine, events, drama, business and celebrities. Working at a flagship store in a major city, lots and lots of celebrities.
Shortly after I began working there, I got a call at the end of a day. It was a producer from the "Late Show with David Letterman." He was going to be filming a week's worth of shows in Chicago and they were doing a bit with Dennis Rodman who, at that point, was with the Chicago Bulls and constantly in the news. In particular, he was getting quite a bit of press for his dressing in drag gimmick.
The Letterman show had a sketch planned for one of the Chicago shows where Rodman was going to give Letterman a tour of Chicago.
The wondered if we wanted to be a part of it. The next day.
Um, yeah!
The idea was for them to film the two guys walking into the Marshall Field's State Street store, cut the shot and show them leaving with Rodman in drag.
I made arrangements to close off a corner of the store towards the end of the day and met the crew.
Shortly thereafter, Rodman and Letterman showed up. Rodman wasn't really so keen on their idea anymore. He was claiming not to really be in a drag kind of mood. Pretty much pitching a giant diva fit.
Talking with the producers, I threw out the idea that maybe he'd be willing to do it if he weren't the only one in drag. Could we get Dave in a dress, too?
They jumped on it and, in no time, we had Letterman on board to put on a dress.
I ran up to the plus size department and found a dumpy, shapeless shift to put on him (the guy is tall).
We were now running out of time and Rodman was starting to get antsy.
Within minutes, Letterman had changed into his dumpy dress in the security office and Rodman was in his over-the-top drag dress.
I opened the office door and they got ready for the shot.
It was them I realized that Letterman's dress had the security tag still hanging near the neck of his dress. He stood there as I tried to get the clamp close enough to him to remove the tag. It wasn't working.
And then I did it.
I turned to him and said:
Mr. Letterman, I either need you to bend over or take off your dress.
His eyebrows went up into his hairline.
No! No! No! I didn't mean that. Take it back! Take it back!
I am pretty sure I just propositioned David Letterman while he was dressed in drag!
He opted to take off his dress.
I quietly removed his tag and he got dressed.
Neither of us spoke.
I sheepishly left the room.
They filmed the bit. He gave me back my dress.
And I did the walk of shame back to my office. Used dress in hand.
A week later this hat arrived in the mail without a note or anything.
Yup, pretty sure I propositioned David Letterman and all I got was this hat.
I searched long and hard for the video of the entire segment, but I couldn't find it. The best I could do was this clip which, unfortunately, ends just before the bit: