When Ray Padgett attended his first Bob Dylan concert at Chicago’s Aragon Ballroom in 2004, he walked out feeling more than a little confused. He was just 18 then and expected a traditional oldies revue much like the Simon and Garfunkel reunion tour stop he’d seen the prior year. “I thought I’d see Dylan sing ‘Blowin’ in the Wind’ while people held up lighters and sang along,” he says. “I don’t need to tell you that it wasn’t like that. I don’t think I loved the concert, but I was very intrigued by it, and I wanted to learn more.”
He started by finding the setlist online, and downloading all of the songs via the Napster clone Kazaa. His only knowledge of Dylan’s music at that point came from a couple of Sixties records from his dad’s collection, but suddenly he was discovering a whole other side to the catalog in songs like “Every Grain of Sand,” “Summer Days,” “Cat’s in the Well,” and “Million Miles.” “I listened to that 17-song playlist over and over again,” he says. “Through that, I got into Bob Dylan.”
His interest grew into an all-consuming obsession once he discovered the vast world of Dylan live recordings, which he chronicles in lovingly obsessive detail on his subscription-based website/newsletter Flagging Down the Double E’s. It’s been online for a mere five years, but it’s already become one of the key hubs for Dylan discourse and information on the Internet alongside Karl Erik Andersen’s Expecting Rain, Bill Pagel’s Boblinks, and the late Olof Björner’s About Bob.
Unlike those sites, which largely provide setlists, fan forums, news updates, discographies, and recording session logs, Flagging Down the Double E’s focuses entirely on Dylan as a live performer. It’s updated almost daily with comprehensive analysis of recordings from 1961 all the way through the most recent stops on the Never Ending Tour. There are also special projects that dive deep into everything from the first week of the 1966 tour with the Hawks to Dylan’s 1995 run of shows with Patti Smith. Amazingly, there’s even a 176-song collection spotlighting the best version of every original tune performed on the Never Ending Tour.
Editor’s picks
Just a few months after launching the site, Padgett started conducting original interviews. The expansive chats with Dylan band members like Larry Campbell, David Mansfield, Jim Keltner, and Benmont Tench were eventually assembled into the 2023 book Pledging My Time: Conversations with Bob Dylan Band Members. And he’s also spoken with fringe figures, like 1990 audio tech Brian Willis (“I got yelled at for interacting with him”) and 1978 crew member Marshall Bissett (“his internal metronome is impeccable”), who have never talked publicly about their experiences.
We chatted with Padgett, 38, about his long history of Dylan fandom, the creation of Flagging Down the Double E’s, how he’d design a Bootleg Series centered around the Never Ending Tour, and many other hopelessly geeky Dylan topics.
What’s the earliest music you liked as a kid?
The earliest music that felt like my own was Weird Al. That was something I got into at 13, the same age everyone gets into Weird Al, if you’re a nerdy, inside boy who doesn’t get enough sunlight. And I became a big Weird Al fan.
What came after that?
Honestly, probably Bob Dylan. I was into other things spread across the board — I had a little Weezer phase. But in terms of my obsessive super-fan persona, it was probably Al and then Bob.
What’s your strongest memory from the first Dylan show you saw at the Aragon Ballroom?
The moment was right near the end, halfway through “Like a Rolling Stone,” where for the first time all night, I went, “Oh yeah, I’ve heard this one from before.” The other moment that struck me, and this is probably too, too nerdy, but this was the Freddy Koella era, which didn’t last long. But I remember this weird guy coming, and he was unlike most Dylan guitarists. He would step center stage for a solo. It’s a very un-Dylan band member thing to do. It was this weird guy constantly stepping center stage and making the strangest noises I’ve ever heard. Honestly, I remember him as much, and maybe more than I remember Bob that night.
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How did your Dylan fandom grow after that?
I discovered the online Dylan fandom, essentially. At the time, the message board of choice was the Dylan Pool. I think Expecting Rain existed, but I remember all the energy, or at least all my energy was the Dylan Pool. I discovered trading CD-Rs since the internet at that point was fast enough to find people to trade them with, but not fast enough to trade the lossless files, so I spent a lot of my time packaging CD-Rs into little envelopes and putting them in the mail and opening little envelopes of other CD-Rs.
You clearly had a bigger interest in the live stuff than his albums.
Yes, that is true. I heard all of the Bob Dylan albums…but I’m sure I amassed a small collection of Dylan CD-Rs before I had Down in the Groove. I remember one early official release I got was Budokan, and I got it because I was just getting into Dylan, and I went to the local record store, and that was a two-CD set for the same price, so I got that instead of Freewheelin’. To me, the canonical version of “Don’t Think Twice, It’s All Right” is a reggae song. I heard it that way before I heard the original.
What appealed to you so much about the concert recordings? Some fans are turned off since the audio quality is usually much worse than official releases.
The fact that every one was different and that the same song could sound a hundred different ways on a hundred different nights. I figured that out early on. One of my first CD-Rs was a 1981 concert, which was half gospel, but the other was bringing in older songs and making them sound like gospel songs. I listened to that one a lot.
From day one, I was fascinated both by the mutability of the music over decades, and I liked the fan community. I’d never been a part of that before. And so many fans on the message boards are focused on the live tapes.
There’s also this huge world of Grateful Dead concert recordings, but the band has officially released so many of them officially. In the Dylan world, 98 percent of it is unreleased. You have to hunt around for it. It can be difficult to find.
But if you’re obsessive, if you have that sort of obsessive fan quality like I do, that’s almost a plus that it’s difficult. I wouldn’t have found it that way at the time, but in retrospect, I absolutely think the fact that I was doing all these CD-Rs and printing out janky, fan-made, bootleg artwork… I enjoyed listening to the music, but I enjoyed that side of it, too.
What were your career goals when you were younger?
I don’t think I had a career or goals in mind. I was a religious studies major in college, which tells you how career-focused I was at the time. I didn’t know that music journalist was a career. I had done it since high school. I had written reviews for my high school newspaper, and then in college I ended up editing the small music magazine we had.
A guidance counselor or something was like, “You know, people do this for a job,” and it sort of was a surprise. My college didn’t have any music journalism program. I was practically the only one. After graduating college, I got an internship at Spin, and then I started thinking about maybe I could actually do this.
You also started the Cover Me blog.
Well, after Bob Dylan, I got really into cover songs. I became obsessed with them in college, through Bob Dylan, actually, through him playing one on Theme Time Radio Hour. This was the peak of the MP3 blog era, so I started a cover blog. It got readers, even though it was just me doing it from my dorm room. And eventually, many years later, that sort of turned into my first couple of books [Cover Me: The Stories Behind the Greatest Cover Songs of All Time and the 33 1/3 about I’m Your Fan: The Songs of Leonard Cohen].
What inspired you to start Flagging Down the Double E’s?
I think of it as a pandemic project. By early 2020, I’d sort of fallen out of the world of Dylan. I lived in New York at the time, so I’d see one of the Beacon residencies every year or two, one show, but I wasn’t paying attention to setlists. I wasn’t talking to other fans online. I wasn’t going to Expecting Rain. And I got thinking that I sort of missed that part of my life. It had been a meaningful and fulfilling passion for me. And for no particular reason, I just had sort of drifted away from it.
I got into the New York indie rock scene, and because I’m someone who, when I like music or listen to music, I want to write about it, I came up with this newsletter idea as an excuse, honestly, to start listening to more Bob Dylan tapes again, which I had not been doing for a while.
I didn’t have any grand strategy. I certainly didn’t think I’d be doing it five years later. I didn’t even think I’d be doing it five months later. But the pandemic hit, and I had a lot of time, so I ended up devoting more time than I thought I would very early on.
What was the original concept for it?
Just me writing about Bob Dylan bootlegs without any interviews, which is sort of a big thing now. But for the first year or so, there were no interviews. There was really nothing, except for “Here’s a random Bob Dylan bootleg that, for some reason, I’m writing about on this date.” I often wrote about shows on their anniversaries.
The first few were actually in January, and they were all 1974 and 1998, because those were the only two years he ever toured in January, so I got really sick of ’74 and ’98. I was really writing it almost for myself. I figured I could get the 50 most obsessive Expecting Rain users to read it, and that was enough.
How big is your collection of bootlegs?
I have 956 live tapes in my iTunes. I feel like I’m one of the last people who still uses iTunes, and it’s because of Bob Dylan bootlegs. You’re not going to get them on Spotify, so here I am with this massive collection.
I’ve never been a collector in the sense that I don’t have a ton of rare or unheard stuff. I try to share it if I’m allowed to. I appreciate that you wrote that about those ’76 tapes. My inclination has never been to hoard stuff. It’s to share it and, as a result, most of the stuff I have is stuff anyone could have.
How did you transition from writing about bootlegs to interviewing people?
I was writing about a show in New Orleans around Jazz Fest in 2003. I’m just listening to the tape and within two songs, I’m like, “What the hell is that noise?” It’s a saxophone. I know enough to know that Bob Dylan did not have a full-time saxophonist in his band in 2003, so I go to Olof’s files. I look it up.
It’s this guy, Dickie Landry, who I’ve never heard of. I’m not a jazz guy, so I Google him. He’s still around. He has a website, and just kind of on a whim I emailed him. I was like, “Hey, do you want to tell me about this? Do you remember it?” He replied back, “Sure.”
He has this very charming story about meeting Dylan in a restaurant. He sees [Dylan bassist] Tony Garnier there, who is a mutual friend. Dylan immediately tries to bounce, because he doesn’t like having dinner with people he doesn’t know. Tony convinces him to stay. Bob gets very interested in the fact that Dickie worked with Philip Glass, on and on and on. Eventually, he invites him to sit in, and he sits in for the whole show.
I had no idea this story existed. Dickie had never told the story before, and I’m sure no one had ever asked him the story before, so that was sort of a turning point for me. Then I ran it, and I was like, “All right, this is, even by my standards, fairly esoteric,” and it was easily the most popular newsletter I’d ever done.
It really snowballed from there.
Yeah. One sort of led to another. As I’m sure you know, people are reluctant to talk about Dylan, so a lot of these people haven’t ever spoken about him before. It often takes a long time to get people to say yes. Every time I do one, it makes it a little easier to get the next one. I find every one fascinating, and it has become an unexpected focus of my work, and then turned into the book.
What kind of people are you looking to interview?
First and foremost, band members. My criteria early on, and this is still mostly true, is people who have worked with Dylan in a live capacity. My newsletter…is about Bob Dylan concerts, which is niche upon niche. I’ve expanded a little bit. I’m talking to crew people too, behind-the-scenes people.
Some fans assumed that anyone who worked with Dylan in the last couple of decades signed NDAs. That seems to not be true.
No one has ever mentioned an NDA. It’s just sort of this cone of silence. Everyone knows Bob is private. I’m sure his band members know that more than anyone. No one, understandably, wants to do an interview where some quote gets taken out of context or blown up into a headline that makes either them or him look bad, and they get a call.
I can understand it, so the first dozen maybe, were very, very difficult to get. I had to convince them that I was legit, and that I was going to let them tell their story in their own words, and at length, and not just excerpt some little bit. When I had built up a couple of examples, people could see, “Oh, this guy goes deep. He really knows the music. He’s not just looking for gossip or some sort of gotcha thing or some trivia about Bob Dylan. He’s not going to ask about Bob Dylan’s kids or something.”
At that point, it’s gotten easier to get people to talk and, even though we focus mostly on the music, when you’re talking, you inevitably get funny, charming, whatever, behind-the-scenes anecdotes.
How have these interviews broadened your understanding of how the Never Ending Tour operates?
The biggest thing is just how much work, musically, goes into it offstage, how many rehearsals there are, and how much they’re working on during soundcheck. It struck me talking to more recent band members how intensive the rehearsals are between legs, even when it’s going to be the exact same people playing the exact same songs as they did one month prior. There’s still three days of rehearsals.
I think the presentation of the Never Ending Tour is it just one day rolls into your town and rolls off again like it was just a dream. And so learning about just how much goes into it, just how much Dylan cares about getting every show right, just how much he makes the band work at getting every show right, whether or not they always succeed, that’s something that it’s opened my appreciation for.
You called the year 2000 the best year of the Never Ending Tour. Why?
It’s the year I’m most jealous I didn’t see. I wasn’t a fan by then yet. I think I was at end of middle school. And I think that that band, Tony Garnier, of course, and Larry [Campbell], Charlie [Sexton], [David] Kemper, and Bob are just firing on all cylinders. There’s the amazing acoustic sets. They’re doing “Country Pie” electric. They’re doing all these amazing bluegrass gospel covers by the Stanley Brothers. It’s just these beautiful shows, crazy sets.
Some of the first bootlegs I would’ve gotten were rips of the Crystal Cat from fall of 2000. I remember printing out the art for Münster, and Portsmouth, and Cardiff, and just listening to these over and over again.
When I talked to Larry, who was one of my earlier interviews, as I was prodding him, I’m like, “What was your favorite era?” And, honestly, I expected him to say 2000, but he ended up saying 2002, because he loved covering Warren Zevon and the Stones, this sort of later era of covers, which was great, too. That was when they started doing the harmonies with him and Charlie, so it’s opened my appreciation. I don’t think 2000 is best by a mile anymore, like I might’ve with that early newsletter, but it probably still has a special place.
I saw really great shows that year, but my favorites were in late 2002. The thing I miss the most from that time is the harmony vocals Larry and Charlie would provide.
I miss the harmonies, and I miss the guitar solos. It’s funny. It’s like a “grass is always greener” thing, because when Denny Freeman was in the band, no knock on Denny Freeman, who I liked, but Dylan gave him so many solos. Every song had like three different solos, to the point that, even though the solos were fine, it was like, “Jesus Christ, enough already.” Now it’s gone exactly the opposite way, including when he had Charlie Sexton back in the band and Charlie Sexton didn’t do one solo the entire time.
You wrote recently about Dylan’s “Wolfman” era. Tell me about that.
Bob has gone through many vocal inflections, and Dylan fans have come up with clever nicknames for many of them. First was upsinging, which was in the late 2000s, when he would end many lines as if it was a question, going up at the end of every single line over and over again, until it’d become very annoying.
Then, after that, came the Wolfman, which is more or less what it sounds like. Bob’s always a little growly, but this was extreme. Unlike upsinging, this you can pretty much hear on some albums. If you listen to Christmas in the Heart and Tempest, that’s basically Wolfman, and it was even more extreme live.
That’s maybe one of the reasons I fell out of love a little bit at that time. I didn’t think the shows were as good in the 2010s, especially early in the 2010s. Then he starts doing these Sinatra albums. They were almost like singing lessons for himself. He almost uses singing these standards as a way to rehabilitate his voice. His voice in his 80s is way better than his voice in his early 70s was, which is sort of this perverse thing, so the Wolfman went away.
There’s no way of knowing, but some people have speculated he underwent some sort of throat procedure.
Totally plausible. I’ve also just heard he quit smoking again, which also makes total sense to me. But the change is gradual. It’s not like one day he got surgery, and then he sounded much better. I do still think, regardless of the rest of that, that doing those songs where the whole point is to sing, something was brought back out of him.
A real joy for me at shows in the late 1990s and early 2000s was not having any real idea what song he was going to sing next. How have you felt about the recent years where he’s been locked into a pretty tight setlist most nights?
It took me a lot of getting used to. The worst Dylan show I ever saw, in terms of just my own personal experience, was early on in “The Set.” I had unplugged enough that I did not know this was a thing. I saw him in 2013 on back-to-back nights in Hoboken and Jones Beach. The Hoboken one was great, and then I went to Jones Beach the next day, and all right, the first song that they sang was fine. The second song that they sang, it’s not unheard of. Five songs, six songs, 10 songs, I start getting really pissed off. Again, had I been more plugged in, I would’ve known. A huge part of collecting the bootlegs was that every one would have a different set list and different song order.
I do think that contributed to me becoming disillusioned for at least a few years. It took until the Rough and Rowdy Ways tour for me to get into it enough to realize all the many things that do change from night to night. That’s because even when the songs don’t, the inflections, the arrangements do change. One night a song has drums and is a fast, up-tempo song. The next night it’s basically a solo piano ballad, the same song. It turns out, just as much is changing, even though the set list on boblinks.com ends up looking identical.
Right. That’s a fair point a lot of fans miss.
It requires more effort. People need to listen to “When I Paint My Masterpiece” on 2023 tapes and 2024 tapes. One of them sounds like “Istanbul (Not Constantinople),” and the other is a slow piano ballad. I know it looks like it’s the same, but you’ve got to pay attention, and if you do, it’s extremely rewarding.
I know we were both in Milwaukee in 2021, for his first show after the pandemic. That was obviously a very special night. I hadn’t felt quite that way at a Dylan show in a long time.
I’m with you. People often say, “What was your favorite show?” That was mine. It has honestly, almost nothing to do with the music on stage. Is it the musically best show I’ve ever seen? It was very good. I don’t know if it was musically the number one, but it was the emotion in the room. You were there. You felt it.
It seems crazy, even a few years later, to imagine a world where we didn’t know if Bob was ever going to tour again. We didn’t know if anyone was ever going to tour again, but that’s how we lived for the better part of a year. So, just being able to be there, nothing is ever… No matter how good the shows I see in the future are, nothing is ever going to top the feeling of the emotion in that room.
Are you able to imagine a Bootleg Series that chronicles the Never Ending Tour? How would you structure it if you were put in charge?
I have imagined in, and I should be put in charge of it. Convey that I’m joking, but I have thought about it. It’s almost impossible. It would almost have to be one disc a year, which makes it an extremely large box set, but if you’re going to do any justice to it, you have to. 1995 needs its own disc, 2000, 2002…
If you want to do a two-CD Best Of for the casual, that’s fine, but to really do it right, I think each year needs a CD. Honestly, there would be enough excitement in the fan community. I don’t think the price, or the fact that it would be 30 CDs long would be any barrier. People got stoked about the ’74 set, and that’s basically…not the same show every night, but a lot more repeats than you get on a Never Ending Tour year.
Would every year get one great show or a compilation of the best moments?
If I were doing it, I would do a mixture of songs. Just pick the absolute best. It’s much more work, but I think that would be very rewarding.
Do you think that Salt Lake City 1976 will ever surface or it simply doesn’t exist?
I don’t think it exists. I’ve asked so many people that. Obviously, the Archives doesn’t have it. Another fan did a big search for it from the other side, from the ground up perspective, which I thought was a good idea. Maybe some rando Salt Lake City local or dad had a tape in the back of the closet. It made sense, but didn’t turn up anything. I even asked the sound engineer who gave me the other never-heard ’76 soundboards. He doesn’t have it. I’d love to hold onto hope, but hope is fading fast on Salt Lake ’76.
What other tapes do you hope surface in the future?
Oh, there’s a lot. It’s only sort of a show, but the full Masked and Anonymous live sessions. There’s so much more of that than ended up in the film. What’s on the film and what’s in the soundtrack is so good. Again, amazing band and different songs, different arrangements. That alone could be a bootleg series.
I would love for later ’78, like some of those soundboards to get out. Complete Budokan was nice. I’m glad to have it, but half of that was released on the first Budokan and the shows got so much different. Street Legal got into the mix, so I hope Complete Budokan has not closed the door on releasing some actual ’78 soundboards.
I’ve heard that Budokan is one of the only multi-tracks they have from the tour, if not the only one.
I’m sure that’s true, but I have the same skepticism that I have about the DAT tapes or whatever, that a soundboard… It’s like for 99 percent of every Dylan show ever, a soundboard is going to better than what we have now. A two-track or whatever is just fine with me. You’ve mentioned the Grateful Dead. They did a whole series of Dick’s Picks. They did like 40 albums that were all two-tracks or whatever. They were the non-multi-tracks. That was the whole idea behind them, so I think being too precious about that is a shame.
Do you see yourself as a Dylan scholar in the same vein as Clinton Heylin?
No. I still think of myself as a Dylan fan. I wouldn’t use the word scholar. I would certainly not use the word “Dylanologist.”
But you’re doing the work. You’re talking to all sorts of people who have never talked before. You’re moving it forward.
Yes, perhaps a big fish in the smallest of ponds, but yeah I guess someone else might call me that. I think of myself as a Dylan fan, and I’m a Dylan writer, but scholar sounds… I come from a very not-academic place. So much of Dylan scholarship is from academia, and that’s fine. I have nothing against that, but that’s not my background at all, and that’s not how I write or even approach this stuff. I never write about the lyrics. I don’t analyze them. I don’t mention them. I don’t even think about them. I’m just not someone who pays much attention to lyrics. It’s funny to do all this work on Dylan and the thing that most other people focus on I pretty much entirely ignore.
Why is that?
I’ve never been a lyrics person, not for Dylan or anyone else. I’m listening to the performance. I’m listening to how the voice sounds. I’m listening to how the band sounds. I’m listening to the energy. I’m listening to the melody. And the lyrics just sort of float by me. It’s just not where my personal loyalties lie and, as a result, it’s not what I want to write about.
What’s the dream interview that you have yet to book?
Tony Garnier, of course. I don’t even try with the current people. I know they’re not going to talk. They probably shouldn’t talk, so I don’t approach anyone who’s currently in the band. But one day, hopefully, many years in the future, when there’s no longer a Bob Dylan band, I’d love to talk to Tony.
I’m really hoping the real close people like Tony write their books one day.
Tony could write a five-volume set of books. Can you imagine the stories that guy has?
Did you see A Complete Unknown?
Yes. This is a very lukewarm take. I liked it, didn’t love it. I thought the performances universally were very good, the best part of the movie probably. I thought the overall plot and structure was fine in a sort of paint-by-numbers, Hollywood, biopic-y way. I was very skeptical going in, and I was somewhat pleasantly surprised, but my loyalties are with I’m Not There, of course. That’s the Bob Dylan movie for people like me.
I think it’s going to bring new fans to the shows.
It’s getting new Dylan fans, which is great. I certainly hope some of them come to the live show. You do wonder if we’re going to get another wave on the next tour, maybe younger people this time, walking out, going, “What the hell was that?” But hopefully…here’s the optimistic version…I was one of those young people 20 years ago, but even with the, “What the hell was that?” I was a little intrigued, and it sent me down the path to where I am now, so I’m hoping a few of those young people will also use whatever the latest version of Kazaa is to download some Bob Dylan.
Why do you think he does so many shows a year? How much of it is the money and how much of it is passion?
Zero percent is money and 100 percent is passion. Look at the sale to Sony for whatever it added up to. Half a billion dollars, if not more. Lord knows, he does not need the money. Yeah, it’s what he likes to do.
For most people, Bob Dylan will be the albums. He’ll be Blonde on Blonde and Blood on the Tracks and Freewheelin’ and all the rest, and that’s fine. But for us obsessive fans, I think we’re in tune with how he himself thinks of it, which is that the art is created on the stage every night, in the moment, in the room, and then it’s on to the next show.
If you could time travel to any show in history, what would it be?
Rolling Thunder ’75. I’m sure half the Dylan fans would say that, but come on, it’s like four hours, not just for Dylan. It’s like four hours of music. You’re going to get Joni Mitchell and Ramblin’ Jack, and Roger McGuinn and maybe the greatest Dylan performances ever, some of them. Yeah, the Montreal ’75 tape is just amazing, so that would be hard to beat. Or maybe I’d go to Salt Lake ’76 and I’d bring a modern recorder with me. If I can bring gear, then I’m switching it to Salt Lake ’76.
Are you a fan of this current band with Jim Keltner on drums and with one less member?
I was at the first Outlaw [Music Festival Tour] show, which was the first show with this band, which was a wild show. The set list was insane. He’s doing “Cold, Cold Heart.” He’s doing “My Babe.” He’s doing all these covers we didn’t expect, most of which he then immediately dropped after that one show.
But it was also wild in terms of the performance. The band, even though I’m sure they had rehearsed, they seemed under-rehearsed. Tony Garnier was walking around trying to direct traffic the whole time. It was sort of sloppy in an endearing way, in a way I hadn’t seen Bob Dylan be sloppy in many years. Rough and Rowdy Ways is such a perfect presentation [by comparison].
The poster for the Rough and Rowdy Ways tour said 2021 to 2024. Do you think the show will be something different this year?
I think it’s going to feel different, yeah. When those posters first came out, I fully pooh-poohed them. “Whatever, just someone put some numbers on it. He’s doing it to troll us. Just ignore.”
Sure enough, for three years, he plays the same set. With the exception of Outlaw, he plays the same set with a whole bunch of Rough and Rowdy Ways songs every single night, and so I was convinced that he, in fact, had called his shot three years out and that, in fact, just as he promised, he’s ended it. It’s over. Now, I’m not saying he’s never going to play a Rough and Rowdy Ways song again, but I don’t think the next tour is going to be anything like it.
Do you hope to be at the last show, wherever it happens?
I hope it never happens. I hope he outlives me, but yeah, sure. Then again, I hope to be at every show.
