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| 2024 | Starred in the sci-fi thriller film 'It's What's Inside', written and directed by Greg Jardin. |
| 2024 | Gavin Leatherwood appeared in the music video 'Sweet Delusion' by Bella Poarch, playing the love interest role |
| 2024 | Willie Nelson was featured in the 'Smoke Hour ★ Willie Nelson' and 'Smoke Hour II' interludes of Beyoncé's 'Cowboy Carter' album. |
| September 2024 | Following the death of Kris Kristofferson in September 2024, Willie Nelson became the last surviving member of The Highwaymen. |
| June 2024 | Nelson canceled performances at the Outlaw Music Festival due to health complications. |
| March 5 2024 | Nelson received 19 write-in votes for President of the United States in the Minnesota Legal Marijuana Now presidential primary. |
| 2023 | Willie Nelson performed at two concerts at the Hollywood Bowl to celebrate his 90th birthday. |
| 2023 | Willie Nelson was inducted into the Rock and Roll Hall of Fame. |
| 2023 | Willie Nelson was the subject of a five-part documentary titled 'Willie Nelson and Family,' announced for release at the 2023 Sundance Film Festival. |
| 2022 | Willie Nelson released 'A Beautiful Time,' which received nominations for the 65th Annual Grammy Awards, resulting in wins for Best Country Solo Performance and Best Country Album. |
| December 2022 | Mark Rothbaum announced a five-part documentary 'Willie Nelson and Family', set to be released at the 2023 Sundance Film Festival. |
| October 21 2022 | Released debut EP 'Moonlighting'. |
| September 2022 | Nelson resumed his tour after recovering from COVID-19. |
| May 2022 | Nelson postponed several shows after contracting COVID-19. |
| April 8 2022 | Released the single 'Be My Lover'. |
| 2021 | Collaborated with Karen O of The Yeah Yeah Yeahs to perform David Bowie and Queen's 'Under Pressure'. |
| 2021 | Joins the cast of the HBO Max comedy series The Sex Lives of College Girls, expanding his acting portfolio. |
| 2021 | Willie Nelson released 'The Willie Nelson Family,' which received a nomination for the 65th Annual Grammy Awards. |
| October 22 2021 | Released the single 'Driftwood Mermaid'. |
| March 2021 | Nelson recorded a version of 'I'll Be Seeing You' for a public service announcement encouraging COVID-19 vaccination. |
| February 19 2021 | Released his debut single 'Just For Tonight', collaborating with Boom Forest Music, Thomas Dutton, and Gavin McDonald. |
| January 2021 | Nelson and his sister received the Moderna COVID-19 vaccine. |
| 2020 | Concludes his role in Chilling Adventures of Sabrina after two seasons of the show. |
| 2020 | Concluded roles in Wicked Enigma and Chilling Adventures of Sabrina |
| 2020 | Gavin Leatherwood appeared in the music video 'Skin' by Sabrina Carpenter, playing the love interest role |
| 2020 | Gavin Leatherwood appeared in the film 'Bad Therapy', playing the character Spit |
| April 20 2020 | Willie Nelson held a variety show titled 'Come and Toke It,' which was part of a series of livestreamed benefit concerts aimed at raising funds during the U.S. coronavirus pandemic, with some proceeds supporting The Last Prisoner Project. |
| 2019 | Willie Nelson released 'Ride Me Back Home', which charted at number two on the Billboard Top Country Albums chart and earned him a Grammy Award for Best Country Solo Performance for the title track. |
| 2018 | Began starring in Wicked Enigma as Jason in a 3-episode role |
| 2018 | Leatherwood had multiple acting roles including an episode of Time Being as Honest Man, an episode of Grown-ish as Pete, and a role in My Dead Ex as Bryce across 2 episodes |
| 2018 | Begins starring in the Netflix fantasy series Chilling Adventures of Sabrina, a significant breakthrough in his acting career. |
| 2018 | Nelson sang 'Cruel World', written by Daniel Lanois for the video game 'Red Dead Redemption 2'. |
| 2018 | Nelson appeared on 'Restoration', a cover album of Elton John songs, performing 'Border Song'. |
| 2018 | The Texas Institute of Letters inducted Willie Nelson as a member for his songwriting. |
| September 29 2018 | Willie Nelson hosted a free concert in Austin to support Beto O'Rourke's campaign, concluding the event with a performance of 'Vote 'Em Out', which was later released as a single. |
| July 2018 | During his Fourth of July Picnic, Willie Nelson endorsed Democratic Senate candidate Beto O'Rourke, performing a song with him despite facing criticism from conservative followers. |
| June 2018 | Willie Nelson expressed his disapproval of the Trump administration's family separation policy. |
| 2017 | Gavin Leatherwood appeared in an episode of NCIS as Dezic's Son in the episode 'Pandora's Box, Part I' |
| 2017 | Made cameo appearances in television shows NCIS and Grown-ish. |
| 2017 | Nelson appeared as himself in Woody Harrelson's live film, Lost in London. |
| 2017 | Willie Nelson released 'God's Problem Child', which entered the Top Country Albums chart at number one and reached number ten on the Billboard 200. |
| June 2017 | He appeared alongside Merle Haggard in the documentary The American Epic Sessions, performing Haggard's song 'The Only Man Wilder Than Me'. |
| 2016 | Pretty Paper, another collaboration with David Ritz, was published. |
| 2015 | His collaboration with Merle Haggard titled 'Django and Jimmie' topped Billboard's Top Country Albums chart and reached number seven on the Billboard 200. |
| 2015 | Nelson announced the establishment of his own marijuana brand, Willie's Reserve. |
| 2015 | Nelson won the Gershwin Prize, a lifetime award from the Library of Congress. |
| 2015 | Nelson underwent stem-cell therapy to improve his lung condition after years of pneumonia and emphysema. |
| May 5 2015 | His second autobiography It's a Long Story: My Life, co-authored with David Ritz, was published. |
| 2014 | Nelson was part of the inaugural class inducted into the Austin City Limits Hall of Fame. |
| 2014 | Nelson released 'Band of Brothers', which topped Billboard's Top Country Albums chart, marking his first number one since 1986. |
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This contents of the box above is based on material from the Wikipedia articles Gavin Leatherwood & Willie Nelson, which are released under the Creative Commons Attribution-ShareAlike 4.0 International License.