I found out I can access the local bar's TouchTones from my house and my work. So on random evenings, I'll queue a song list up starting with Photograph (my calling card), then do a list of bizarre songs (Surfin' Bird, it's Not Unusual, a 20+ minute Sufjan Stevens song, Babymetal, etc), then close it out with Photograph again.
I'm going to give the bartender a Pavlovian response to hearing Nickelback
So, from experience, I don't think it likes it if you play a song too close to itself. I had a short Playlist once with two or three songs bookended with Photograph, and it dropped the second Photograph. So I'm hesitant to do the same song over and over. Maybe a song that has a whole bunch of different versions might work!