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May 6, 1989Reba McEntire, Kitty Wells and Lyle Lovett guest on TV's long-running "Hee Haw"Oct 13, 1989Singer/songwriters Guy Clark, Joe Ely, John Hiatt and Lyle Lovett perform together for the first time at The Bottom Line in New York. They will periodically revisit their coffeehouse-style gatherings for more than 15 yearsDec 22, 1989Richard Dreyfuss stars in "Always," making its theater debut. The soundtrack features Lyle Lovett's "Cowboy Man," plus music by Jimmy Buffett, Bonnie Raitt, J.D. Souther, The Platters, Micheal Smotherman, The Coasters and Van MorrisonFeb 21, 1990"Lyle Lovett And His Large Band" wins Best Country Vocal Performance, Male, during the 32nd annual Grammy Awards in Los AngelesFeb 28, 1990MCA releases the "Always" soundtrack, featuring Lyle Lovett's "Cowboy Man," plus music by Jimmy Buffett, J.D. Souther, The Platters and Micheal SmothermanAug 7, 1991Lyle Lovett attends the premiere for the movie "The Commitments." The after-party includes a Wilson Pickett performance of "In The Midnight Hour"Mar 31, 1992Curb releases Lyle Lovett's album "Joshua Judges Ruth"May 4, 1992"Dwight Yoakam's in the corner trying to catch my eye/Lyle Lovett's right beside me with his hand up on my thigh": Columbia releases Mary Chapin Carpenter's playful single "I Feel Lucky"Aug 3, 1992The Recording Industry Association of America awards a gold album to "Lyle Lovett And His Large Band"Oct 22, 1992Lyle Lovett sings "The Star-Spangled Banner" before the World Series at Skydome in Toronto, as the Blue Jays host the Atlanta Braves. The Braves win, 7-2, on a grand slam by Lonnie Smith
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