49. Peter Green
Voices-hearing Fleetwood Mac guitar virtuoso
Case History: Fleetwood Mac’s founding member was one of the greatest blues guitarists ever. But after bingeing on acid, he tried to persuade his bandmates to donate their earnings to charity. He quit in 1970. He grew his fingernails extraordinarily long so he wouldn’t have to play guitar again. He then spent 25 years being subjected to electroshock therapy and taking heavy psychiatric drugs that made him sleep 20 hours a day.
Craziest Moment: Was arrested in 1977 after threatening manager Clifford Davis with a rifle; Davis had been trying to deliver a $50,000 royalty check to his London home.

48. R. Kelly
Chart-topping R&B sensation or poster boy for urination? Both!
Case History: He sleeps all day and plays basketball every midnight. He has been known not to change his underwear for days at a time and make his wife knock first before entering rooms in her own house. Then, of course, there’s his alleged enthusiasm for home-video hobbyism — plus those 21 counts of child pornography he’s dealt with.
Crazy Moment: Secretly marrying the 15-year-old Aaliyah probably could have been better thought out.
He’s So Crazy: “Osama bin Laden is the only one who knows what I’m going through.”

47. Jim Morrison
Lived fast, died young, left a (fairly) good-looking corpse…in the bath
Case History: In the ’60s, Morrison’s method of opening “the doors of perception” was to guzzle booze and vacuum LSD and any other drugs he could get his hands on. Was dead in a bathtub by age 27 in 1971.
Crazy Moment: Married a witch in New York City. The happy couple drank each other’s blood as part of a pagan ceremony.

46. Sid Vicious
Insulted fans. May have killed his girlfriend. What a catch!
Case History: On the Sex Pistols’ 1978 U.S. tour, he beat fans with his guitar and carved GIMME A FIX into his chest with glass. Vicious met his match in junkie/lover Nancy Spungen; he was charged with her murder after she was found dead under a sink in a hotel room.
Craziest Moment: Released from detox in 1979, he overdosed on heroin and died in his sleep.

45. James Taylor
Sensitive soul who found comfort in heroin and sanitariums
Case History: Taylor committed himself to McLean Hospital in Massachusetts for depression at age 17; he wrote his first songs during his year-long stint in the psych ward. Three years after getting out, he checked himself into a sanitarium in the Berkshires — this time, he was addicted to heroin.
Craziest Moment: Never really fully mental. His loopiest act was perhaps leaving McLean — gasp! — without waiting the full three days for his paperwork to go through.

44. Chuck Berry
Duck-walked underage prostitute across state line
Case History: Berry was sentenced to three years in jail in 1961 for transporting a 14-year-old prostitute across state lines for “immoral purposes,” and in 1994 he was sued by 60 women for allegedly video-taping them in the bathroom of his Southern Air restaurant in Wentzville, Missouri.
Craziest Moment: Protected himself from allegations of rape by insisting that female fans strip and pose, smiling, for pictures with him before he’d have sex with them.