Tennis:

Bob Dylan’s mysterious motorcycle accident in 1966—an event that has provoked all sorts of wild speculation—gave the overworked mercurial star an opportunity to become a full-fledged recluse, which he seemed to need, whether it was warranted by his injuries or not. He skipped out on Woodstock, turned his back on the flower power rock scene, and in 1967, recorded what I consider his absolute best album,John Wesley Harding (go ahead and yell about my tastes in the comments). By 1969, he had recovered enough musically to expand his palate and record my second favorite of his albums, the full-on country Nashville Skyline. He had also recovered enough physically to play tennis with George Harrison, as you can see below.

Bob Dylan and George Harrison playing tennis, Isle of Wight, August 29, 1969.

source : https://www.openculture.com/2013/09/bob-dylan-and-george-harrison-play-tennis-1969.html

Pool

Bob Dylan playing pool, in 1964 Kingston, New York , Photo by Daniel Kramer.

Chess

it appears that Bob Dylan was also a keen chess player. In the Bob Spitz biography, there are several paragraphs describing how Dylan used to try to psyche his opponent out by talking during the game. He also was known to do the same wild, nervous leg shaking motion while playing that he does when he is singing. There is also a report that Dylan’s manager paid Bobby Fischer so Dylan could play chess with him.

In the Bob Dylan art gallery online, one of the artists has done a sketch called “Only a Pawn in their Game” with Dylan playing chess, the title being taken from a song in the album “The Times They Are A-Changin’ (Jan. 1964). Also, if you have the issue of MOJO with Dylan on the cover there is a beautiful picture of him playing chess.

This photograph of Bob Dylan playing chess is just one of many snapped by Daniel Kramer who enjoyed extraordinary access during the prime of Dylan’s career. Kramer’s collection is coming to Hibbing, Minnesota this year for Dylan Days and through the summer. PHOTO: Daniel Kramer

Here’s a picture from the 27.09.12 Rolling Stone Interview with Bob Dylan, nary a word in the entire interview about this interesting picture of Dylan seated before an empty chessboard with Anatoly Karpov looking on in the background.

source : https://www.chess.com/forum/view/general/does-bob-dylan-play-chess

The above, to which we shall return soon, was one of many photographs of Dylan in Woodstock taken byDaniel Kramer in 1964 and 1965. On the left is Dylan’s roadie Victor Maimudes. But as we all know only too well, being a chess player, and describing oneself as such, is far, far less about playing and more about that intangible state, both overwhelmingly joyous and depressing, whereby the game begins to dominate your waking thoughts, your bookshelf, your life. What interests me is that in the early-to-mid 1960s chess continues to crop up as a minor motif in Dylan’s work

Bob Dylan and The Band – Playing Chess- Tour 1974

Backgammon

Bob Dylan Playing backgammon 1975 , on the Rolling Thunder Revue tour

Bob Dylan plays pinball

Bob & Levon, Playing Ping Pong

Bob Dylan. And Levon Helm. Playing ping pong. In the 70s. In what looks to be the bowels of an arena. With a sweet ass cop wagon in the background. The only other person to play ping pong in white heeled leather shoes may be Prince.

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