10. David Bowie/Nine Inch Nails (1995)
In the summer of 1995, Trent Reznor hit the road with his lifelong hero, David Bowie. It was an interesting time for both artists: Nine Inch Nails were at their absolute peak and David Bowie had been on a steady career nosedive for a decade. Nine Inch Nails were drawing much larger crowds than Bowie, but Reznor still opted to open up the show. Fearful of the young fans leaving in droves, Reznor decided to bring Bowie onstage towards the end of the Nine Inch Nails set for a few duets that led directly into Bowie's headlining set. Making matters even more complicated, Bowie had sworn off performing his greatest hits earlier in the decade. He still played older songs, but they were relative obscurities like "Joe the Lion," "Andy Warhol" and "Teenage Wildlife." Despite Reznor's best efforts, many fans left before the show was over.
At the time, the tour seemed like a bit of a disaster; in hindsight, it was an absolutely stunning show that suffered only from bad timing. When Bowie went back on the road in 1999, he brought the hits out of retirement. Nowadays, of course, both acts have retired from touring altogether, making this 1995 tour seem all the more amazing.