I think it's a tie between Depeche Mode and the B52's. Both three times.
Edit: The mention of Barenaked Ladies reminded me that I've seen the Dave Matthews Band and/or Barenaked Ladies about 3,000 times (but only when I was in college) and does it count if you don't really remember?
I also saw the band Phish like 20x but that was bc I just followed my older sister around to get out of the house when we were teens.Never really got into music that doesn’t involve singing for long periods of time
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