Bob Dylan ended the 1900s on a bit of a downswing. In the midst of a four year drought where no new albums were released (and his only new song in 1999 was a redone version of “Chimes of Freedom” with Joan Osborne). There wasn’t much to report about all year.

Of course, Dylan toured relentlessly, because that’s what he does. Indeed, in 1999 he performed 119 concerts – a new Dylan record! These were broken up into five distinct tours:

January – March   US Winter Tour   28 shows
April – May   Europe Spring Tour   21 shows
June – July   US Summer Tour with Paul Simon   38 shows
September  US Fall Tour with Paul Simon  10 shows
October – November  US Fall Tour with Phil Lesh  22 shows

Notably, 1999 was the year that Bucky Baxter left the Never Ending Tour (in May), replaced by Charlie Sexton. Sexton had one hit in 1985 (“Beat’s So Lonely”) and has toured with Dylan from 1999 to 2002, from 2009 to 2012, and from 2013 to today. I already miss Bucky Baxter on the slide guitar, though there are some interesting new arrangements and solos that Sexton has brought to some familiar songs. Life moves on.

The shows that I listened to all week were from all June and July (the tour with Paul Simon). It was an unusual tour, and clearly a nostalgia tour for the most part. The AP story about the announcement called it “nirvana for 1960s folk fans” and noted that each man would play a 75 minute set each night, flip-flopping the opening/closing spot. This was the first tour for Simon since 1992, with the AP noting that Simon had spent the last few years working on “the Broadway flop The Capeman”, which is something that I have never heard about in my life.

Let’s start with Simon. I used to have no strong feelings about Paul Simon. Like every other white person on the planet, I owned a copy of Simon and Garfunkel’s Greatest Hits and I think that The Graduate has a great soundtrack. I kind of liked Garfunkel better than Simon, but if I’m being honest that’s just because Carnal Knowledge is such a great film. I hated the Paul Simon of the Graceland period, when it was inescapable on the radio, and his decision to break the cultural boycott of South Africa was simply unconscionable. Simon has “no regrets” and my feelings haven’t changed either – I think he’s a scumbag.

So. Here he is touring with Bob Dylan, playing to the nostalgia crowd (the bank managers super-show, as my wife just put it). Someone has nicely put together a lovely little two CD bootleg called Boys in the Bubble that includes selections from various shows with each performing solo, and a few of them playing together. It’s a well done set (they’ve even included Dylan and The Grateful Dead doing (badly) “The Boy in the Bubble” from 1987 (they can’t remember all the words), and a 1992 Dylan cover of “Homeward Bound”). Each disc opens with one man introducing the other for his set, which is a nice little touch.

The duets are probably the most notable things here. There are six of them:

“I Walk the Line” and “Blue Moon” from Mountain View. In Virginia Beach they did “That’ll Be the Day” and “The Wanderer”.  “The Boxer”, which Dylan (horribly) covered on Self-Portrait, is included from Dallas, “Forever Young” (tried only one time) from Denver, “The Sound of Silence” from Concord, and “Knockin’ on Heaven’s Door” from Austin. The crowd goes crazy virtually every time – waiting for that magical moment, but it never really comes. Here’s a version of “Sounds of Silence” that is as good as they got together. It’s fine, but Dylan is no Garfunkel, so there isn’t a lot of effective harmonizing. In general, none of the duets are very good – but they’re better here than they are on any of the Dylan songs:

Generally speaking, Dylan performed far more interesting sets than Simon did. Simon does his hits. Dylan did “Highlands” (the whole song!) and “Down Along the Cove”. There is no question that Dylan is the more interesting artist at this juncture by a wide margin. Evidence of this can be found on best four shows from the tour where Simon doesn’t appear. These are collected in a five CD bootleg titled Ace of Clubs, because Dylan was playing small venues (Tramps in New York City the night before a Madison Square Garden show with Simon; Bogart’s in Cincinnati and so on). These shows are fantastic (except for the occasional idiot fan whooping and hollering, but what can you do?), and consistently a lot stronger than the big stadium shows. Dylan’s band is much more interesting when they’re trying to fill a small room than when they’re in full rockstar mode of any venue with a name like Coca Cola Star Lake Ampitheatre, Pepsi Arena, or Nissan Pavillion. I’d really recommend the Ace of Clubs collection as the highlight of the year, and I’d suggest simply skipping the Paul Simon shows.

I do wonder if Dylan and Simon are genuinely friendly. He seems to appreciate him on stage (Dylan is terrible about faking things like this). On the other hand, Simon did write this anti-Dylan piece in 1965:

Rank jealousy.

In the 1960s I’d have put Simon a step below Dylan, but at least in the same ballpark. In 1999? It’s not even close – Simon is the anchor dragging down the summer Dylan shows.