January 12: Bob Dylan’s “Strangest and Longest” Concert Ever


Today in 1990, in a final warm-up, or perhaps the kick-off,  to a  tour that would see him present multiple concerts in the United States, Brazil, France and England in under 30 days, rock legend and Nobel Prize laureate Bob Dylan played what one reporter called “the strangest and longest show of his career”  before 700 historically lucky fans at Toad’s Place in New Haven. Expected to only play one set when the normally reclusive and audience-shy singer stepped on stage at 8:45 pm, Dylan surprised everyone when he offered to do a second set, then a third , and finally a fourth,  concluding  the unprecedented performance at 2:20am.  The last song, the classic  “Like a Rolling Stone,” had been preceded by a figurative  “last call” from the bar more than hour earlier. Because state drinking laws  required  establishments serving alcohol  to close at 1am, the waitstaff had collected all the drinks from the tables  before the final set began.

Dylan and back-up  guitarist G E SMith (a New Haven native), bassist Tony Garnier and drummer Christopher Parker performed a total of fifty songs that night, which covered the entire gamut of Dylan’s career. The uncharateristically outgoing and relaxed performer also took requests from the audience and played covers of songs such as Bruce Springsteen’s “Dancing’ in the Dark,” Hank Williams’ “Lonesome Whistle,” and Joe South’s “Walk a Mile in My Shoes.”  Overall, the concert lasted four hours and fifty minutes. Commenting on a bootleg audio tape of the performance, reviewer Wade Tatangelo  wrote “a good portion of the this show sounds like Dylan, perhaps a bit tipsy, doing karaoke, and it’s a joy to hear.”  Another reviewer wrote, “This is the kind of concert you need to listen to at least once in your lifetime to understand why people love Dylan so much.”

Dylan’s  performance added luster to the already sterling reputation of Toad’s Place as one of the nation’s great music venues. The York Street music emporium, in the shadows of  theYale campus, had hosted The Rolling Stones in what music critic Randall Beach has called the greatest rock concert in Connecticut history in August 1989.  Though its 700 person capacity makes it a relatively small venue for major acts, its reputation has long helped it punch above its weight in its ability to draw name performers.  In 2015 USA Today named Toad’s Place the best small music venue in the country.

Dylan’s January 1990 concert at Toad’s Place lives on in an audio tape of the  performance that has long circulated on the internet. It is a lasting tribute to one of the greatest, longest, perhaps strangest, and certainly most memorable musical events in Connecticut history.


Further Reading

Large Dave, Bob Dylan’s longest show ever was at New Haven’s Legend at Toad’s Place ” i95rock.com

Randall Beach, “Looking back at the greatest rock concerts in Connecticut history,” ct insider

Bob Dylan’s Set list from the Jan 12, 1990 Concert at Toad’s Place ,” Setlistfm

Brian Steinberg, “The Attraction of Toad’s,” Yale Alumni Magazine