In August 1964, twenty-one-year-old photographer
Douglas R. Gilbert, on assignment for
LOOK magazine, photographed an up-and-coming folk singer named Bob Dylan. Just twenty-three years old, Dylan had already composed a striking body of work, including "
Blowin' in the Wind," yet he himself was still relatively unknown.
All that was about to change. For more than a week, Gilbert photographed a surprisingly open Bob Dylan, smiling and relaxed among friends like musician John Sebastian and poet Allen Ginsberg. To Gilbert's dismay,
LOOK deemed Dylan's appearance "too scruffy" for a family magazine, and the images remained unpublished and unseen, until now.
![](https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEgWY5OxbJKjZeMEIotvp_jsBDBDa4tvt3LXhAnmC1n5EuRWYLpL3NfnW9pYk68x0fP1VssHFT-POxiYbkUvdPgOMlqbwM7zaSlOCFxObyCRmU2PYT0mX097v1o9YkV-r7elv5ZtPb4aDHet/s1600-rw/Bob+Dylan+by+Douglas+Gilbert,+1964+(1).jpg) |
(left to right) Mason Hoffenberg, John Sebastian, Bob Dylan and Victor Maymudes, Cafe Espresso, Woodstock, NY |
![](https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEg3pZ1j82Bdlzi2bN4v86ce6jcjiMRgfVdvSyOAMnDEPXPpng6ySv1W6tF1aiIr7Ag44A4e6WyJHhK_yPOtnrYj6SNM7OayDA_nhe9G2MsChD5ehXCe9VOwosfvhUvGfmqwo8Wu5pTThcID/s1600-rw/Bob+Dylan+by+Douglas+Gilbert,+1964+(2).jpg) |
Bob Dylan jammin' with John Sebastian, Cafe Epsresso, Woodstock, NY |
![](https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEj56CGKvjLKW0EqEFqpbJ_NFXuN88ZVmYYUN0mnD0vKxC1bJR0TJ2spH7O9iaL4DXxwOCJF4TuaszJRDxiOKjQwkMH2-or_AmeBFH0PiBYAKshNex30e4JLK45J7-ErKt_LHGGuly9t0B3k/s1600-rw/Bob+Dylan+by+Douglas+Gilbert,+1964+(3).jpg) |
Bob Dylan lighting up at the Kettle of Fish Bar, Greenwich Village, NY |
![](https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEjaJuSD1vISS4U-ArxWla6Hnz5UuQjATHI-D8UdWNEO4z4TYfgSR9_lTNblLlbNu18u9PdUCZi3ODTeZPzF1NbuxaaryxD6NseMY1Pgki9NqId75JNzmiTys5VIxNxPPaEJ5a58E8tLWIm9/s1600-rw/Bob+Dylan+by+Douglas+Gilbert,+1964+(4).jpg) |
Dylan at the Kettle Of Fish Bar, Greenwich Village, NY |
![](https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEitkf7zx_3I1rgQlGNs2ziNgorkyiPhl6x0O81632k6GTbE2jbM8sD-oP7NPC7WTa9PSgpqJqQBUgKREJl0liTv12kgUQF89_1MhFgpEfwWsHaTfzYCjLZ6a9iAt_TjNka1tEMdy8bjABqe/s1600-rw/Bob+Dylan+by+Douglas+Gilbert,+1964+(5).jpg) |
Bob Dylan at home, smoking in yard, Woodstock, NY |
![](https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEi76hJWpoZioge66ZPIbQ5wcRVhNWeZX7qndMb0aox0BHJGpXASWnNgqd99oK2U1oOxYKUYhzUPlSR6AhJcR0rt9tZAeB1sDFCmGU4K9bS-udgPIa5SwNeMY0bDs8aWzf7LSWpSF21BImB7/s1600-rw/Bob+Dylan+by+Douglas+Gilbert,+1964+(6).jpg) |
John Sebastian & Bob Dylan jammin' at the Cafe Espresso, Woodstock, NY |
![](https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEh79kc5CE79oqhNPFs06lMvYBgzlcjl-Xe1AEHDnI7OBV_IK6HdY_HQA0GWf16YEQWUSELj6eQ3IqnMuSnIZt0xkgg0Ds1wLgVSA71AHPVRPEdOOuQmtpY5HegbFvzM_N5pnTqK7nhAHNS7/s1600-rw/Bob+Dylan+by+Douglas+Gilbert,+1964+(7).jpg) |
Bob Dylan on Triumph, behind Cafe Espresso, Woodstock, NY |
![](https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEgof7km8sHEt236mg5TKD0aUoemZQb2YZnPeUl1vK1Ya0xXKRCbmnOHKLpwTydepyIZL2Eiy4AAUva2B4_0pH99icyMy73pbp4tYypaGk91874epUzDrIjlsU0mVCet2NnBtHfJKuatdtUE/s1600-rw/Bob+Dylan+by+Douglas+Gilbert,+1964+(8).jpg) |
Bob Dylan at home waving to poet Allen Ginsberg, Woodstock, NY |
![](https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEhz1K6oA8w30Jo9SgG6iY1eaWhzcNbe3mmKLL6cyFa7JBbaTrfszyVFeWmXQPPKuJV2kqqwhATLhFwlYLiVLpG3HApO3gdHiQ3FSc5Cq1fBxT3pn7xGUrx2T1yTjzfLLElMue-uw8u3dmtL/s1600-rw/Bob+Dylan+by+Douglas+Gilbert,+1964+(9).jpg) |
Bob Dylan behind the Cafe Espresso in Woodstock, NY with the daughter of Bernard and Mary Lou Paturel (owners of the cafe) |
![](https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEj4iQMkqRNUuHjPszwtn2gjUc-AZHK0EywFLaq8wxNM-xUoG3KKQZzW1P1tF2x4F_mnpUZzAzE5CfKaeyc_kNdLJ5fORI6qBJ0ARfYKSsdHSaucLvk6U9dEEJjZ-KyZ8SHubXcX7Ci58WU4/s1600-rw/Bob+Dylan+by+Douglas+Gilbert,+1964+(10).jpg) |
Bob Dylan and Joan Baez performing at Newport Folk Festival, Newport, RI |
![](https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEgpy3QCBHgzArzdIJOOrONEKANyG4VFYU_qrOUHDN1vnzTckO5cJW4LS5Dq6w03FqhKAxBTtaSL2QtO5GD4GqP4qvD0ieua2l7_FCQH3V2zuQrAIuHmPYwkeF5zI9s5slw3S6gj_siADcEP/s1600-rw/Bob+Dylan+by+Douglas+Gilbert,+1964+(11).jpg) |
(left to right) Mason Hoffenberger, John Sebastian, Bob Dylan at Cafe Espresso, Woodstock, NY |
![](https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEiSQVIriCrRcM1FmxG4Eun1eBavV0mNcADofxN6pskG8lGZDsmvmUvKjikoRWQzJvKis_OMO7Y9AihsLWZftmNDy0CVqt4nGjq4_Xl_zh4dFdrOcv3nV68WkJu-xwo2R89tubMQO8OWOfkW/s1600-rw/Bob+Dylan+by+Douglas+Gilbert,+1964+(12).jpg) |
Bob Dylan in yard at home, Woodstock, NY |
![](https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEi2bDCc3agAh40uXbgI9fdA4i7um6ZdWsPzzBLxTbHu2UzjiXDnwSODj-C7sjzl9Ns1jMasVicQ2mSvp8MtrCEwRmHnEoQHBPLbKbP7IS5gWKyFa3P2kS_ek44C6TQZ6BId5LRktzxdRq_V/s1600-rw/Bob+Dylan+by+Douglas+Gilbert,+1964+(13).jpg) |
Bob Dylan watching Dean Martin at home, Woodstock, NY |
![](https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEgbENqiZp1dN-VNZO0pvGe-i-oK_S1T-cJzR-Pei5tNjf3Y1tr9LnoOnyYjT0GNwkpjctMsrTwo_VA5xjYICKjcC10hA0tq5kuz93QelFdenA-R1O4YU-Fr5FF2I30PmMp4LeRCSNlvieBJ/s1600-rw/Bob+Dylan+by+Douglas+Gilbert,+1964+(14).jpg) |
Bob Dylan, John Sebastian and the Paturel clan, Woodstock, NY |
![](https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEi0ZEgeZR7kCJZXXrQtuDElV2XZK-h5rWl9b20XW-ISmtgb-LL1hHnHDPJd3gccfhMBDTfJrcOpF72vT7POrfiCGzBaZDwLnFaIn8HlfUGqLeEdqwPScGd1Gr5cVl74Yg1Fdw5uulbZMB9j/s1600-rw/Bob+Dylan+by+Douglas+Gilbert,+1964+(15).jpg) |
Bob Dylan and Ramblin' Jack Elliot in Greenwich Village, NY |
![](https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEhCBP0rWqn38hYVk2yiDy3h4wUf2XY5rOVIlTrunp9-QzMoHsGOPBT9iIBvP6l89MAPVftXry2H3U4sBVQwnkm21DCsZT6SbQdBnwYve-GhygkXLqToZkKLoWFLVBPhWUsgi8XbQwZLHTPX/s1600-rw/Bob+Dylan+by+Douglas+Gilbert,+1964+(16).jpg) |
"Take one now, the pictures already framed" Bob Dylan, the Kettle of Fish Bar, Greenwich Village, NY |
![](https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEgvONYaY1Z_abN-LiHWeZj_ZtHjF2uGNRj1dHNddZVRswIgZwZTSU0GL7unL-kOTEk7jJvu3lpo3i_lv128TW8Y9t6qvyDoM9fkX62kHRKkQ59aV_GZJiNw7yoy_R5AQdJwfK5KNeIwZqmS/s1600-rw/Bob+Dylan+by+Douglas+Gilbert,+1964+(17).jpg) |
Bob Dylan in bookstore, Greenwich Village, NY |
![](https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEhpyoal9nsyjDt-GVtnH5-PGmAdfOisxHgcR2wlytVHJL_5lIWHo4p8PcKZRVlEwCGJBlJN_a9qfBZGy_Mdrn-REOxN_PaYz6JIjLZTDNnd_9k2dktnZ1VBixg2MvtYS7pOKMv59bPC4iSh/s1600-rw/Bob+Dylan+by+Douglas+Gilbert,+1964+(18).jpg) |
Bob Dylan, day performance at Newport Folk Festival, Newport, RI |
(Photos ©
Douglas R. Gilbert)