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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 above.
Harrison, meanwhile, had quit The Beatles in January, then was coaxed back into the band, which more or less broke up later that year. But he had been busy—recording two mostly-instrumental solo albums and writing his Hindu gospel hit “My Sweet Lord” and the rest of his incredible 1970 triple album All Things Must Pass. Somehow amidst all the turmoil and transition, as Harrison began his most productive solo period and Dylan prepared to release what nearly everyone considers his worst record, Self Portrait, the two found time to hit some balls before Dylan’s performance at the Isle of Wight festival. Dylan was apparently a longtime tennis fan. His 1964 “I Shall be Free No. 10” contains references to the sport. The photos were released by the Harrison family for the 2011 Martin Scorsese-directed doc George Harrison: Living in the Material World (trailer below).