I'm enjoying the hell out of a great new book that was just released called "The Legendary Toad's Place - Stories From New Haven's Famed Music Venue." I recently had the pleasure of interviewing the co-authors of the book, Toad's Place owner Brian Phelps, and Reporter/Journalist Randall Beach. I had to ask them about one of the chapters in the book, which is devoted to something that I never knew -  The longest concert that Bob Dylan has ever played, 4 hours and 20 minutes - 50 songs - happened at Toad's in January of 1990.

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The longest concert that Bob Dylan ever played happened exactly 5 months after one of the most famous rock concerts in Connecticut history - The Rolling Stones - which had also taken place on Toad's stage. Legendary Connecticut concert promoter Jimmy Koplik was friends with Dylan's manager, and had called Jimmy thinking about having Dylan doing a warm-up show for his upcoming tour. Toad's had just hosted the Stones, so...

750 tickets were sold out in 18 minutes.

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Getty Images

The promoters were expecting Dylan to play one set, but they had no idea what they were in for.

Dylan brought longtime SNL band legend G.E. Smith, who is from New Haven, as well as Tony Garnier, and Christopher Parker to back him up. The band came onstage at 8:45 PM on Friday January 12, 1990, and opened up with a cover of Joe South's "Walk a Mile in My Shoes." After ripping through a first hour-long set of his hits, and some obscure catalog selections, Dylan came off stage at 9:40 PM.

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Getty Images

I spoke with Toad's Place's owner, and the author of the book, Brian Phelps, who told me this:

"Dylan asked me if he could play another set? And we said sure go ahead!  You know, and they asked again, and played a third. Can I play another? You know what? Yeah! go ahead! There's no Problem!  He wasn’t sure what he was going to play, it was like a practice session, because he was going on this theater tour. I think most of the theaters  were 5000 seats on up, and our show was like a practice session… well for him anyways, but for the people that were there, they were just loving it, and they really couldn't believe it. I actually gave the whole rundown to his son Jakob, from the Wallflowers, who have played Toads a number of times, and I told him about his father’s show. He started peppering me with questions about it, and he really enjoyed the whole story about how it happened, and the length of the show, and everything that went on that night. He was a great great guy too. Jacob enjoyed the history of the club, and the history of playing in the same place where his father played his longest show in."

Bob Dylan took requests from the crowd at Toad's Place that evening, playing Bruce Springsteen's "Dancing in the Dark," Hank Williams' "Lonesome Whistle," and even a Traveling Wilbury's song "Congratulations."

Getty Images
Getty Images

Dylan's fourth and final set began at 1 AM, and Toad's had to shut the bar down at AM due to state law. Instead of stopping the show, they just collected all of the drinks from the crowd, and Dylan finally wrapped it up with his Masterpiece "Like a Rolling Stone" at 2:20 AM. Dylan threw his harmonica into the adoring crowd, and walked off after 4 hours, 20 minutes - 50 songs. Still the longest show that Bob Dylan has ever played.

Bob Dylan's Setlist from his night at Toad's:

  • Walk a Mile in My Shoes
  • One More Cup of Coffee
  • Rainy Day Women #12 & 35
  • Trouble No More - Muddy Waters cover
  • Been All Around This World
  • Political World
  • Where Teardrops Fall
  • Tears of Rage - The Band cover
  • I Dreamed I Saw St. Augustine
  • It Takes a Lot to Laugh, It Takes a Train to Cry
  • Everybody's Movin' - Glen Glenn cover
  • Watching the River Flow
  • What Was It You Wanted
  • Oh Babe, It Ain't No Lie - Elizabeth Cotten cover
  • Lenny Bruce
  • I Believe In You
  • Man of Peace
  • Across the Borderline - Hyatt,Cooder,Dickinson cover
  • Leopard-Skin Pill-Box Hat
  • All Along The Watchtower
  • Tight Connection to My Heart (Has Anybody Seen My Love)
  • Political World (Revised)
  • What Good Am I
  • Wiggle Wiggle
  • Stuck Inside of Mobile With The Memphis Blues Again
  • Paid the Price - Moon Martin cover
  • Help Me Make it Through the Night - Kris Kristofferson cover
  • Man in the Long Black Coat
  • Congratulations
  • Dancing in the Dark - Bruce Springsteen cover
  • (I Heard That) Lonesome Whistle - Hank Williams cover
  • Confidential - Sonny Knight cover
  • In the Garden
  • Everything is Broken
  • So Long, Good Luck and Goodbye - Weldon Rogers cover
  • Where Teardrops Fall
  • Political World (Revised)
  • Peggy-O
  • I'll Remember You
  • Key to the Highway - Charles Segar cover
  • Joey
  • Lay Lady Lay
  • I Don't Believe You (She Acts Like We Never Have Met)
  • When Did You Leave Heaven - Jimmy Scott cover
  • Maggie's Farm
  • Been All Around This World
  • In The Pines
  • Highway 61 Revisited
  • Precious Memories - John Wright cover
  • Like a Rolling Stone

I want to thank Brian and Randy again for taking the time out of their day to talk with me, and I highly recommend The Legendary Toad's Place: Stories From New Haven's Famed Music Venue. It's packed full of interesting stories about the Connecticut treasure, and the wide range of artists that have graced the stage at 300 York Street in New Haven over the decades.

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