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    • Sep 22, 1987
    Steve Earle records two songs for the "Planes, Trains And Automobiles" soundtrack: "Continental Trailways Blues" and a remake of the 1963 Dave Dudley classic "Six Days On The Road"
    Nov 12, 1987
    Steve Earle's wife, Lou, catches him with another woman in Los Angeles. The Earles are separated the following day, and Lou begins divorce proceedings
    Nov 25, 1987
    "Planes, Trains And Automobiles" debuts in movie theaters, with Steve Martin and John Candy in starring roles. The soundtrack features Steve Earle, Emmylou Harris and Ray Charles, among others
    Dec 22, 1987
    Steve Earle has his third child, Jessica Montana Baker, born in Johnson City, Tennessee, to a groupie, Theresa Baker
    Dec 31, 1987
    While fighting with a crew member in a Dallas hotel, Steve Earle is accosted by a policeman, who chokes him with his night stick. Earle is jailed for aggravated assault, and his voice is forever changed by the incident
    Apr 13, 1988
    Geffen Records employee Teresa Ensenat quits her job in Los Angeles and moves to Nashville to be with her boyfriend of three years, Steve Earle
    May 16, 1988
    MCA releases Patty Loveless' "A Little Bit In Love," written by Steve Earle
    Jun 11, 1988
    Alabama hosts June Jam VII in Fort Payne, Alabama. The lineup features Restless Heart, Exile, Carl Perkins, Steve Earle, K.T. Oslin, Eddy Raven, The Bellamy Brothers, Sawyer Brown, Mel McDaniel, Sweethearts Of The Rodeo, The Shooters, Dan Seals and Ricky Van Shelton
    Jul 22, 1988
    Steve and Lou Earle's divorce is finalized, with the singer required to pay her $2,500 monthly in alimony and child support, plus legal fees and $5,300 for her other debts
    Sep 13, 1988
    Steve Earle is arrested by mistake in Michigan when a bondsman errantly determines he has jumped bail. Earle is jailed for several hours until the matter is resolved
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