The unforgettable night Bob Dylan and Bruce Springsteen spent at Frank Sinatra’s house
For both Bob Dylan and Bruce Springsteen, Frank Sinatra was their icon. Even though they were from different generations, their love of Sinatra was a bond which bridged the age divide between the songwriting pair. Dylan and Springsteen may well have been their own icons by this point; however, one night in the 1990s, they were fortunate enough to spend a night in his company. The duo went to the legend’s house for dinner and it was as magical as they anticipated.
Dylan has never shied away from his admiration of Sinatra, and in 2015, he released an album of songs connected to ‘Ol’ Blue Eyes’ titled Shadows Of The Night. “When you start doing these songs, Frank’s got to be on your mind. Because he is the mountain. That’s the mountain you have to climb, even if you only get part of the way there,” he told The Guardian.
Likewise, Springsteen has always outwardly expressed his appreciation for his fellow Jersey native. In an appearance on Stephen Colbert’s chat show in 2021, Springsteen even declared ‘Summer Wind’ by Sinatra as his favourite song of all time. While meeting his hero could have been awkward, thankfully, it was a dream-like experience for ‘The Boss’.
In 1995, Dylan and Springsteen joined forces to pay tribute to Sinatra in a TV special to celebrate his 80th birthday. Dylan performed the deep cut, ‘Restless Farewell’, which the octogenarian had requested, while Springsteen offered a rendition of ‘Angel Eyes’.
Around this time, both musicians were invited to Sinatra’s house for a celebratory dinner. During the evening, he pulled Dylan aside and told him a key nugget of wisdom that stayed with him. In conversation with Bill Flanagan in 2017, the singer-songwriter recalled: “I think he knew ‘The Times They Are a-Changin” and ‘Blowin’ In the Wind.’ I know he liked ‘Forever Young,’ he told me that. He was funny, we were standing out on his patio at night, and he said to me, ‘You and me, pal, we got blue eyes, we’re from up there,’ and he pointed to the stars. ‘These other bums are from down here.’ I remember thinking that he might be right.”
Meanwhile, in Springsteen’s autobiography, Born To Run, he recalled how he, and his wife, Patti, befriended the Sinatras. They regularly attended parties at their house, and there was one occasion when Dylan also was there, which provided Bruce with a memory that’ll stay with him until he draws his final breath.
“Sometime after dinner, we find ourselves around the living room piano with Steve and Eydie Gorme and Bob Dylan. Steve is playing the piano, and up close, he and Eydie can really sing the great standards. Patti has been thoroughly schooled in jazz by Jerry Coker, one of the great jazz educators at the Frost School of Music at the University of Miami,” he recalled in his book. “She was there at the same time as Bruce Hornsby, Jaco Pastorius and Pat Metheny, and she learned her stuff. At Frank’s, as the music drifts on, she slips gently in on ‘My One and Only Love.'”
Springsteen continued: “Patti is a secret weapon. She can sing torch like a cross between Peggy Lee and Julie London (I’m not kidding). Eydie Gorme hears Patti, stops the music and says, ‘Frank, come over here. We’ve got a singer!’ Frank moves to the piano, and I then get to watch my wife beautifully serenade Frank Sinatra and Bob Dylan, to be met by a torrent of applause when she’s finished. The next day we play Frank’s eightieth birthday celebration for ABC TV, and I get to escort him to the stage along with Tony Bennett. It’s a beautiful evening and a fitting celebration for the greatest pop singer of all time. Two years later, Frank passed away, and we were generously invited to his funeral.”
Listen to Springsteen’s favourite song of all time, ‘Summer Wind’, below.
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