The first person Steinberg and Kelly offered this to was Peter Kingsbery, a singer from Texas who was in the band Cock Robin. Says Steinberg, "We heard Cock Robin play live and this guy Peter Kingsbery had this great voice very much like Roy Orbison - it's a powerful voice. We thought, 'Wouldn't it be great if he would sing I Drove All Night, so we invited him over to Tom's house where we had a studio. Peter was a good guy, a little bit arrogant. He heard the song and he liked it, but he said, 'Well, I'm a songwriter myself. Why would I record one of your songs?' it was a nice meeting, but he didn't have any interest in recording our song."
On February 9, 1987, Steinberg and Kelly saw Orbison perform at a supper club in Lakewood, California called The Hop. Says Steinberg, "When we walked in, the place was jammed and most of the people there were middle-aged women. At that time Roy hadn't had a record on the charts in many years. He did not have a recording contract. Roy hadn't been heard from in a long time. The band went up on stage, Roy was not in sight and there were a couple of background singers. The band starts playing and the girls start singing the intro to 'Only the Lonely.' I sort of braced myself. I said to myself, 'His vocals on his records are so otherworldly and so unbelievable that there's no way the guy's going to walk in this club and sing those songs like he did on those records.' Roy Orbison walks out and he sang 'Only the Lonely' and he sang all his hits and if it's possible he sang them better than he did on his records. It was just unbelievable. It was one of the great moments in my life, just to be there in this small club and hear Roy sing one hit after another. When the show was over, Tom and I wandered outside and there was his trailer. Of course, we were hoping to meet Roy. We didn't, but we met somebody who I guess was Roy's manager at the time. We mentioned we had written a few hits and were Roy Orbison fans. Not much came out of that, then for some reason I went into a studio called Record One in Sherman Oaks and Roy Orbison was in there recording. I went up to him and said, 'A few months ago Tom and I heard you play at this club and you were so good.' We kind of connected and somehow we arranged that he would come by Tom's house and do some work with us and that maybe we would write together. We had already written 'I Drove All Night.' We had a demo of it with Tom singing it. Tom and I walked out and were standing out in the street. We looked down the street and we saw in the distance a red Ferrari convertible coming up the street and we both knew that had to be Roy Orbison. He was driving slowly like someone would who was looking for a street number. As the car pulled up, we saw a guy with big black sunglasses, black hair, and there on a residential street in Woodland Hills was Roy Orbison getting out of his red Ferrari to work with Tom and me. Working with Chrissie Hynde, the Bangles or The Divinyls is one thing because those are people of my generation, but Roy had been a childhood idol. Roy was somebody whose songs just changed my life when I was a kid, so to have him standing there as a peer, someone I was going to work with, my knees wanted to buckle. We walked into Tom's house and there was the idea that we could write something together and he just didn't seem to really want to start writing a song, so rather than write something we said, 'Well, we've got a song that we think you could sing really well,' and we played him 'I Drove All Night.' He said he liked it. Tom played either piano or guitar and taught him the song. Roy stepped up to the microphone. We all had headphones on and Roy sang two takes of the song. Tom and I had written into that song a section that goes, 'Uh-huh, yeah,' and when Tom sang it on our demo we would laugh because Tom was blatantly trying to sound like Roy, and then when Roy did it, it was a moment that was just unbelievable because Roy did it like it was supposed to be done. Roy did those two takes of the song and I gave him some song lyrics. He took them with him with the idea that he might write something to them or that we could work on something in the future. So we had this demo of Roy Orbison singing 'I Drove All Night,' but Roy didn't have a recording contract at the time and Tom and I didn't have the wherewithal to do anything with Roy Orbison's version of the song. We couldn't sign him to a recording contract or promote him or anything at that point in time. We didn't know what to do with it. By that time 'True Colors' had been a big hit for Cyndi Lauper and she had expressed an interest in meeting us and in writing with us, so Tom and I flew to New York and we took with us the demo of 'I Drove All Night' sung by Tom because we figured that she could sing it well. We wrote a couple of songs with Cyndi and we presented this song 'I Drove All Night' to her and she liked it and immediately went about recording it. Tom and I even participated in demonstrating the song to a couple of musicians that she worked with. She recorded it and it came out on her record called A Night to Remember (1989)."
Later in 1987, Roy Orbison got a recording contract with Virgin Records. Working with Jeff Lynne, he recorded the successful comeback album Mystery Girl
, which contained the hit 'You Got It.' He also joined The Traveling Wilburys with Lynne, Tom Petty, George Harrison and Bob Dylan. Sadly, Orbison died of a heart attack on December 7, 1988. Says Steinberg:
"From afar we sort of watched Roy's career come back. We were pleased for him but we didn't participate because all the great admirers of Roy had started to come out of the woodwork. People like Jeff Lynne, Bruce Springsteen and Bono. He didn't exactly need Steinberg/Kelly when he had people of that caliber wanting to work with him. Roy died and a number of years went by. Tom and I took our demo of 'I Drove All Night' to Jordan Harris, who was an A&R guy at Virgin. We got to know Jordan because we worked with The Divinyls, who were signed to Virgin. We said to Jordan, 'Did you know Roy did a version of I Drove All Night early on?' And he said, 'No, I had no idea.' We played it for him and he said, 'We want to make a record of the remaining masters that we have on Roy. We'd love to use that.' Our demo had been a very rough 16 Track affair. We gave it to Jeff Lynne and Jeff rebuilt the track around the vocal that we had cut on Roy. That was very satisfying for us." (Check out our interview with Billy Steinberg