Eastwood has directed Freeman in three of his films, including 2004’s ‘Million Dollar Baby’ and 2009’s ‘Invictus’
On Monday, Oct. 14, Freeman, 87, and his producing partner Lori McCreary shared a photo to Instagram of Freeman posing with Eastwood, 94, and a third man as he wrote that he presented Eastwood with an award at the 2024 Monterey Jazz Festival at the end of September.
“It was a great pleasure presenting my friend, Clint Eastwood, with the inaugural Clint Eastwood Award for Cultural Leadership at the @MontereyJazzFestival last weekend. Clint is a true musician: pianist, composer and a jazz aficionado!” Freeman wrote in a caption to his post. “We had a wonderful time listening to the incredible music of Kyle Eastwood and Mavis Staples!”
Eastwood, best known for his legendary work in Hollywood as an actor, writer, director and producer with four Academy Award wins, sits on the Monterey Jazz Festival’s board of directors, according to its website. Eastwood’s oldest son Kyle, 56, performed at the California-based jazz festival on Sept. 29 with his project Eastwood Symphonic, which featured a jazz quintet performing with an orchestra ensemble that played music from his father’s movies. The festival also included a conversation with Kyle regarding his work in film and music and Clint’s movies.
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Producer McCreary, who co-founded the company Revelations Entertainment with Freeman, additionally shared a photo to Instagram of him and Eastwood posing together at the festival back on Oct. 3 and wrote she had a “fantastic time” at the festival.
Eastwood and Freeman go back a long way; the pair costarred in Eastwood’s 1992 Western Unforgiven, and they reunited again on screen in Eastwood’s 2004 boxing drama Million Dollar Baby. Eastwood directed Freeman once more in 2009’s Invictus, in which Freeman portrayed the late South African president Nelson Mandela.
This is not the first occasion that Eastwood has been honored at the Monterey Jazz Festival. Back in 2007, the Berklee College of Music granted Eastwood an honorary doctorate degree during the festival, citing his interest in jazz through his film soundtracks, individual work as a composer and documentaries Eastwood has made about major figures in jazz.
Even at 94, Eastwood is preparing to release his most recent movie as a director, Juror #2, in select theaters on Nov. 1; the film stars an ensemble cast including Nicholas Hoult, Toni Collette, Zoey Deutch, Kiefer Sutherland, Gabriel Basso, Leslie Bibb, Chris Messina and J. K. Simmons. Eastwood last released a movie in 2021 with Cry Macho, which he also starred in.
Freeman also continues to act frequently, having appeared in two movies in 2024, including My Dead Friend Zoe and Gunner.