Joni Mitchell wrote "Both Sides Now" at the age of 22 while she was still just working in folk clubs and hadn't released a single of her own, much less an album. The lyrics were inspired by Saul Bellow, she explained in an interview to a radio show in 1967: "I was reading a book, and I haven’t finished it yet, called Henderson the Rain King. And there’s a line in it that I especially got hung up on that was about when he was flying to Africa and searching for something, he said that in an age when people could look up and down at clouds, they shouldn’t be afraid to die. And so I got this idea 'from both sides now.'”
Dave Von Ronk was the first singer to cover "Both Sides Now" (under the title "Clouds"), although he seems almost comically inappropriate for its sensibility of girlish indecision. Joni was at a bar in Greenwich Village in May 1967, reeling over a breakup, when she met the session musician Al Kooper, who was crashing at the time at Judy Collins' apartment. Joni and Al got to talking, and she told him he wrote songs. After the bar closed, the two of them went to Joni's apartment so she could play him some of her stuff.
"Her songs were incredible and totally original," Kooper said. "She would finish one, and I would say: more, more. One song especially killed me: 'Michael from Mountains.' I thought it would be great for Judy." Even though it was three a.m., he told Joni they had to call Judy Collins and play her this song.
Judy Collins remembers that Kooper had other things on his mind as well. "I've just met this girl here in the bar," he recalls Al saying. "She and I were talking and she told me she wrote songs. She's good-looking and I figured I could follow her home, which couldn't be a bad thing no matter how you look at it."
Judy remembered Joni playing "Both Sides Now," and instantly recognizing it as "absolutely mind-boggling." The song first appeared on Collins' 1967 album Wildflowers, but was remixed several times before it was released as a single in October 1968. It became Collins' first hit single, rising eventually to Number 8 on the Billboard pop charts. (I've seen reports that Mitchell didn't like Collins' version, but they've also been friends for about 50 years now, so she couldn't have hated it that much.)
Mitchell's first album, Song to a Seagull, came out in March 1968, before Collins' cover of "Both Sides Now" appeared. After the song became a hit, Joni's own version appeared on her second LP, titled Clouds after you-know-what. All told, "Both Sides Now" has been covered a whopping 1250 times, which seems almost unbelievable, but Joni's website has a list of all 1250 artists, including Chet Atkins, Harry Belafonte, Bing Crosby, Blossom Dearie, Neil Diamond, Stan Getz, Dizzy Gillespie, Robert Guillaume, Hole, Carly Rae Jepsen, KC and the Sunshine Band, Willie Nelson (who had an album titled Both Sides Now), and Frank Sinatra.
But the definitive version will always be Judy Collins'. "Some people are bound to sing certain songs," Collins said of the three a.m. phone call from Al Kooper. "It was instantly obvious to me that 'Both Sides Now' was my song." Here she is: