When I was in high school, a kid gave me this Velvet Underground tape. It was the first two records, dubbed onto a cassette pretty carelessly, with songs cutting off at the end of sides A and B. The kid who gave it to me was a fellow guitar player, but a lot cooler than me. He was a slouchy guy with greasy shoulder-length hair, and he told me stories about the Velvets tuning all their strings to the same note, or physically carving the frets out of the necks of their guitars so they could slide dissonantly between microtones during guitar solos. I put the tape on and it sounded like what I imagined taking drugs (a lot of drugs) felt like. It scared me. And it made me want to take drugs, which also scared me.

I recognized the Dylan influence in Lou Reed’s voice, but everything else about him was completely alien. He sounded like he was just talking. He was often out of tune. He sounded like he wasn’t particularly trying to impress anybody. There was something about the music that felt wrong, like it shouldn’t have found its way into a legitimate recording studio. All the rules I thought had existed in music suddenly felt arbitrary and meaningless. I was pretty sure I hated it, but for some reason I kept listening.

Eventually I started to like it, and then there came a day when I realized that the Velvet Underground and Lou’s solo work were the only music I had consistently listened to for the past six or seven years. Other bands had cycled through my stereo, becoming obsessions for a year and then ending up back on the shelf, but I kept listening to the Velvet Underground, every week, sometimes every day. There was a period of about a year where I would wake up each morning and immediately blast White Light/White Heat at a painful volume. It made me feel purified, like I had stripped all my skin off and was now just white bone—nothing could hurt me and I was ready for anything.

I had a band by this point, and was living in Austin picking up shifts at video stores and getting fired and quitting odd jobs, trying desperately to make ends meet and still be able to work and hopefully go on shoestring tours. Nobody knew who we were and it seemed like the people who did know who we were didn’t like us. People particularly seemed to dislike my voice. I had problems with pitch and I couldn’t do the slick things other singers could do. I was trying hard to believe in myself. When people attempted to make me feel better, they would bring up my idol and say, “Well, look at Lou Reed. He’s got a really unconventional voice but it’s original and that’s what some people love about it.” It was a flattering thing to say, but I tried not to entertain any illusions that I was going to ever be even a fraction as successful as Lou Reed.

This was in the days before iPods, when bands would sit in a van on those six and nine and fourteen hour drives between gigs and actually talk to each other, about anything and everything, and would bring boxes of CDs with them and wear the same ones out until certain albums became the official band anthem, some musical spell that would shield and protect you out there, lonely and sick and dirty and hungry on the road. Jonathan Meiburg was our keyboard player and the nearest thing I had to an artistic partner, and our years in close proximity had caused certain things about our personalities to bleed together. Jonathan and I would listen to Berlin over and over again and shudder at the sad and scary parts, and cackle with delight about much of the rest. We loved that record’s gonzo mix of batshit drums, demure woodwinds, heavenly choirs, harmonized guitar solos, the lyrics about speed and suicide and abandonment and breaking people’s arms, and producer Bob Ezrin’s children howling with psychic pain because he supposedly set up some mics and then told them their mother was dead and hit “record.” We loved how Lou rhymed “vial” with “vile.” The last couple songs on the album were like going to church, but a church where they tell you there’s no God and no meaning to anything and then they kick you out. We would always be silent when we got to those last three songs, and we’d be silent after they finished too. We drove across the desert and listened to “Sister Ray” at eardrum-shredding volume, and the landscape outside looked like the landscape inside. That music changed something in us and changed what we wanted to be. We didn’t want to make people happy. We wanted to make people hurt. We wanted to make music for adults, music that didn’t lie to you and feed you a line of shit. And then if we did make happy music, that happiness would have a genuine impact on people because it would be real happiness, happiness that coexisted with the real knowledge of pain. That happiness—like the happiness in “Sweet Jane”—wasn’t false. It was something you could really hold on to.

People still didn’t really care about my band, and by this point I had given up on having a stable place to live. I put all my possessions in storage because I couldn’t afford to pay rent, and I couldn’t keep a job because I was on tour so often. Again, I took comfort from Lou. I thought about how Berlin singlehandedly burnt up all the commercial momentum and public goodwill he had earned from Transformer, apparently on purpose. I thought about stories of the engineer who recorded “Sister Ray” hating the song so much he left the building and told the band to just come find him to stop the tape when they were finished playing. Whether or not I was lying to myself, Lou made me feel like my path was noble. Still, by the time we made our third proper record Black Sheep Boy, I told myself that if nothing happened with it I would stop trying to make a living out of music.

Black Sheep Boy took a long time to gather any kind of momentum, but it ended up being more successful than anything we’d done before. Some people finally knew who we were. Some people even liked us. I still got criticized for being a bad singer, but for every negative review there would be a positive one, more or less. I felt, to some extent, like the work I had been doing for the past seven years hadn’t been a waste of energy.

I was driving across the West Texas desert again, this time by myself, taking a long solo road trip to visit friends and to write. At the end of a long drive day, I checked into a dismal hotel, figured out the wireless password, and wearily started downloading e-mails. And then I saw something I never imagined I’d see, that I never would have allowed myself to picture even in a grand private fantasy. It was an e-mail from a manager who represented Lou Reed. He told me that Lou loved my band and asked if I could call to discuss something.

I’ve read and re-read that short little e-mail more times than I can count. I felt like I was dreaming. I called the number Lou’s manager had written in the e-mail. I haven’t told many people this because I figured maybe I would get in trouble for saying it, but when I called the manager back he talked to me about the possibility of making a collaborative album with Lou. I felt like they were fucking with me. It was the single most validating moment in my musical life. My personal idol had just reached out about working together. I saw everything I was doing in a different light. In the days following the phone conversation, I felt a confidence growing in me that was unlike anything I’d known before. At the same time, I was terrified. The manager asked me to put some ideas together to send to Lou. I had no money to demo anything so I went over to a friend’s house who had ProTools on his computer and some microphones, and I recorded a bunch of stuff I was working on that I thought he might be interested in. After I was done, I played the songs back. With just me and an acoustic guitar, everything sounded so lame, the opposite of what Lou Reed would be interested in. Just some warbling 30-year-old schmuck with his acoustic guitar. But I thought maybe Lou would at least like the subject matter. There was a song about a bunch of sailors who keep a mermaid they’ve captured in a tub on the deck of their ship so they can rape her. There was a song about the mother of the porn star Savannah flipping through old baby pictures after her suicide. I passed them along.

I didn’t hear back. Maybe this was because Lou didn’t like the recordings, or maybe it was because there was other stuff happening in his life. I’m not sure. He made a meditation CD and then eventually did do a collaboration, with Metallica. I’m ashamed to say I haven’t heard it but all the indignant reactions I’ve heard have the Lou Reed fan in me assuming I’d love it. What did eventually happen was that Lou picked us to open for him at the dedication of a venue in New York called the High Line Ballroom. We flew the band up from Austin, loaded in, and watched him do a fabulously cantankerous soundcheck, with John Zorn casually dropping in and jumping onstage. His show was lugubrious and doomy, with a lot of material the audience didn’t seem to recognize. People talked through most of his set and acted like they didn’t care about him, and the feeling seemed mutual. His band was incredible, slick but also murky, dark and malicious-sounding.

After the set, I mustered up my courage to go say hi. Antony of Antony and the Johnsons led me into the central cell in a honeycomb of dressing rooms, each smaller and more exclusive-feeling than the last. I was steeling myself for an uncomfortable or even unpleasant experience. I’d heard the stories of young artists telling Lou they’d been inspired by him and him responding, “Oh yeah? Kill yourself.” Instead, my first sight of an offstage Lou Reed was him gliding across the room into Laurie Anderson’s arms, like a little boy whose mom just showed up to pick him up from school. He constantly doted on Anderson, and smiled with the small handful of friends in the room, and posed for pictures obligingly. He had the aura of a kind, gentle man with a very gentle, almost feminine quality. I’ve told this story to friends many times since and nobody believes me, but that’s the way he seemed. Maybe that was a side he only showed to people with whom he felt comfortable, I really don’t know. I remember a quote from Nico, talking about her early relationship with Lou and saying he could be so sweet, like a little boy, and I like to think that that was the side of him I was seeing, the side of him that wrote “Candy Says.”

When my turn came to talk with Lou, he gave me a soft handshake that he held for an uncomfortably long time. Eventually I had to extricate my hand from his. He told me, “You are a great rock singer. You’ve got a great rock voice. You can sing anything.”

Everything in my life changed when Lou Reed, my musical hero, said that to me. Everything I’ve had the guts to do as an artist since 2007 came out of that moment. I am a different artist now. It was one of the kindest and most perfect three sentences anyone could have uttered, and coming from Lou Reed its effect was profound. I transformed into something else once he spoke those words to me.

Lou said some other things, sweet things and funny things and things I’ve forgotten. When he got to Scott Brackett, our trumpet player at the time, he did the same weird not-letting-go-of-his-hand thing post-handshake and Scott decided to ride it out and spent several minutes holding hands with Lou Reed while Lou had a conversation with somebody else in the green room. Everyone loves that story. But the warmth I felt in that room stayed with me for all the years after, and I still feel it right now.

As it happens, right now I’m on tour, sitting in the back of a Chevy Express van riding from Vancouver to Spokane. I’ve had my data plan on my phone turned off to save money, so I have been slow at keeping up with news. This morning on the hotel lobby internet I saw that Lou had died and had one of those reactions—maybe you had it—where at first I thought it was a joke I just didn’t understand. When I realized it was real—this had really happened—I felt that same thing I’d felt when I got that first e-mail from Lou’s manager, that this must be a dream. Only now I felt it in a horrible, sickening way. I’ve spent the day in a fog. This can’t be real. Lou Reed can’t have left. John from Gawker wrote me and asked me if I wanted to say anything, and writing this has given me something to do. I didn’t fact-check anything I wrote, except for the stuff that happened to me, which I don’t need to fact-check because I’m never going to forget it. Maybe some of my Velvets stories are Lou apocrypha. Google them if you want. I kept them in because this is what Lou fans do—pass stories around that maybe happened and maybe didn’t.

We’re passing through Seattle now, and listening to Berlin, and the experience of hearing Lou’s voice, with all that extra gravity it has right now (put on Berlin right now and you’ll hear it: Lou sounds different), has me hovering just under a full body sob. If I think about the fact that Lou’s gone just a little bit more I’m going to cross over that line and probably start crying in front of my bandmates, and I’m trying not to, so maybe I should stop this piece right now and just shut up and listen.

Will Sheff is the songwriter and lead singer for Okkervil River. He is currently on tour in support of the band's new record, The Silver Gymnasium. He last wrote for Gawker about Dr. Hook and the Medicine Show.