Bob Dylan concerts 20 years apart

Bob Dylan plays in Chicago tonight; 20 years (almost) to the day that I saw him playing in Chicago on Halloween. I’m not there tonight, but I did get to see him twice last week. There’s something about a big, fat, round number like TWENTY years that makes me feel nostalgic about that show. Things have changed since then, for Bob and for me, and those changes aren’t bad.

Seeing Bob at the University of Chicago Pavillon in 1999 was a trip. He was touring with Phil Lesh and Friends at the time, so there were a lot of Grateful Dead fans in the audience. Earlier that day, my travel companion and I figured many of the crowd would probably be dressed up. So we stopped at the dollar store to see what we could find. A pair of fairy wings for me, and a sheriff badge, cap gun and a Lone Ranger mask for my partner in crime. We were sleeping in a minivan and eating peanut butter sandwiches to afford the trip. Our meager costumes were nothing compared to the elaborate costumes some concert goers created. One I remember vividly: A One Night Stand.

During the Phil Lesh set, I recall leaning over and asking, “Is that Steven Wright on the side of the stage?” My travel buddy, shrugged it off. It could be him, but having never seen him in person it’s hard to say for sure and just what the heck would Steven Wright be there for. Just around the time we were expecting Bob and the band to arrive on stage, Steven Wright came to center stage. Yes, Steven Wright of “a lot of people are afraid of heights. Not me. I’m afraid of widths.” It was truly surreal. It was also an A-Ha Moment. Around that time, Bob would introduce his band and was occasionally telling a joke. “Tony bought a bike for his wife. He thought he got a pretty good deal.” A lot of the crowd would groan at those jokes or wouldn’t be paying enough attention to catch them, but I adored them.

In 1999, it was exciting to see several nights of Bob Dylan shows in a row because the setlist often changed nightly. Each night you could expect a couple solid covers, several songs from Time Out of Mind, a couple of the standards, and then it was anybody’s guess what he was going to play. For example, of the 14 songs played on October 31st, 1999, 5 of them were different than the show two days earlier at Miami University.  By industry standard, that’s an astounding variety between shows. Now his set lists rarely alter. But what they lack in originality from night to night, he and his band make up for flawless performances every dang song.

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Set list courtesy of

In Mankato, MN last week, every song was near perfection, sung with feeling and often rearranged to bring out a different nuance of the subject matter.  Jon Bream of the Star Tribune described Bob’s performance in Mankato as, ‘unquestionably forceful, easily understood (no mumbling) and terrifically musical.”

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Set list courtesy of

Some people might think that seeing the same concert multiple times might get boring, but there’s always something slightly different or small gesture to catch. I love watching the band peer over Bob’s shoulder to figure out what he’s going to do next. I was told I had the biggest smile on my face during the entire set in Mankato. And that’s no surprise to me. I enjoyed Milwaukee’s show two days later only slightly less, but that’s more due to having significantly superior seats in at the show in Minnesota.

Bob in Mankato 2019
No photos during the performance or you’ll get in BIG trouble.

Bob has grown out of playing a different set list every night and telling jokes. Instead he has worked hard with his band to put passion into every song and deliver on a stellar show every night.

Show 96 and 57
My concert sidekick.

I’ve grown out some things, too. The days of sleeping in mini vans and eating mostly peanut butter sandwiches to make a tour are past me. I think back to those road trips and those concerts with adoration and awe. AND I’m pleased with the way things are right now, too. I still love seeing Dylan and his band perform and I still have a great traveling partner for it all. Thanks Jeremy. xo


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