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Tim Buckley
The old adage "like father, like son" certainly applies here. A beloved folk-rock singer with a vocal range of five and a half octaves, Buckley rode a wave of commercial and critical success in the late '60s and early '70s. Increasingly influenced by psychedelic and avant-garde music later in his career, he released several experimental albums that tanked. Crushed by their failure, he turned to alcohol and drug binges, finally overdosing on heroin in 1975. Son Jeff would tragically follow a similar trajectory 20 years later.

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Michael Lohan
When it comes to courtroom appearances, Michael Lohan ranks second only to Robert Downey, Jr. The father of DUI-collecting pop tart Lindsay served two years of a four-year sentence for drunken driving, contempt of court, and assaulting his brother-in-law with a shoe. Wife Dina alleges in divorce papers that Michael abused her and that he once told a security guard, "O.J. Simpson has nothing on me. I know exactly how I'm going to kill [them]. I know when I'm going to do it, and I'm going to enjoy it." Add to that his arrests for violating a restraining order (twice) and dine-and-dashing on a $3,800 hotel bill. He even penned a jailhouse song to Lindsay, titled "Confessions of a Broken Heart," in a letter to New York Daily News columnist Lloyd Grove: "I loved and protected you, I was THERE through it all./I do admit, I did at times fall./But these things you know were due to "THEM"/The ones that want to have a piece of my gem!" No surprise that Lindsay is so often on the sauce these days.