On this day in 1990, Bob Dylan played the longest show of his career

Dylan was booked to play a regular show at a popular club called Toad’s Place in New Haven, Connecticut. The show was expected to be a big attraction as the 750 tickets sold out in just 18 minutes, with promoters and patrons alike anticipating that Dylan would play his usual hour long set.

Dylan appeared on stage at 8:45pm, and as expected played an hour long set to an adoring crowd, coming off stage at 9:40pm. However instead of packing up, he approached Toad’s Place owner, Brian Phelps, and asked if he could play another set, a request Phelps gladly accepted. After another hour he returned and asked to play a third set, and then an hour later, a fourth. Finally, after 4 hours and 20 minutes, Dylan threw his harmonica into the crowd and left the stage for the final time at 2:20am.

While the audience enjoyed the show, Dylan himself had to come up with a 50 song set, which he achieved with a number of covers, including some outside of his usual repertoire. One such song  was Bruce Springsteen’s Dancing in the Dark, believed to be the only Springsteen song covered by Dylan. Other featured artists amongst the covers included Muddy Waters, Glen Glenn, Kris Kristofferson. Songs from The Band and The Traveling Wilbury’s also appeared.