Flagging Down the Double E's

Flagging Down the Double E's

Charlie Sexton Makes His Dylan Debut

1991-10-25, City Coliseum, Austin, TX

Ray Padgett
Nov 10, 2025
∙ Paid

October was so busy I never got to the subscriber-requested shows that month. So today, belatedly, the first of three in a row! Thanks to the requesters for the patience (or for forgetting I’d promised to do them). Reminder to everyone else that assigning me a show is a perk of an annual subscription.

How’s this for a historic moment? Charlie Sexton has played 1,256 shows with Dylan. Today we hear the very first one: A brief sit-in in Austin in 1991. (Thanks to Eric for the request).

Sexton was just 23 years old at the time of the show, but he was already a music veteran. This SPIN magazine cover came over five years earlier, when he was just 17.

Wow, what a crazy fluke that Charlie Sexton was on a magazine cover in 1986 right? Think again. In 1986, Charlie Sexton was on a lot of magazine covers.

(That isn’t even all of them by the way. Charlie Sexton was, to quote Tom Waits, big in Japan.)

That same year, 1986, he appeared in Rolling Stone many times as well. Not on the cover, but inside. This one’s my favorite because…well, look who’s in the photo right next to him!

He’d play with Dylan not too long after, of course. And as for Bowie…we’ll get there.

By 1991 though, his fifteen minutes of fame as a new wave rock star were already beginning to fade. He would soon transition into a more stable career path for a guitar genius: Sideman to the greats. Dylan for many years starting in 1999, Elvis Costello currently.

Dylan was aware of Sexton during his initial burst of magazine-cover fame. In 1985, Sexton released his much-hyped debut Pictures for Pleasure, which featured the Top 40 hit “Beat’s So Lonely.” That same year, Dylan released his Biograph box set. In the liner notes, he was asked about new music he liked. Bob answered, in part:

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