A decade plus ago, there was little expectation that Crowell would at one point rule the charts based on his lack of success commercially. Of his first eight singles, the highest charting song was "Stars on the Water" (number 30) in 1981.
But then came a 1988 duet with his then wife Rosanne Cash, "It's Such a Small World." It was his first number one song.
But it would not be his last. Pulled from his biggest selling album ever, "Diamonds & Dirt," (which is being reissued in February as part of Sony's American Milestone series), number ones continued for Crowell with "I Couldn't Leave You If I Tried," "She's Crazy for Leavin'," "After All This Time" and "Above and Beyond."
Five number one hits. The first time a male country singer ever accomplished the feat. Since then, Clint Black is the only other artist to match Crowell.
When asked if he had any expectations "Diamonds & Dirt" would do so well, Crowell says, "None. Just another day at the office. You can never plan. I thought it was special because I had so much fun at the time. I wasn't particularly attached to any outcome, nor did I expect the outcome. That was a pleasant surprise."
One would have thought Crowell would be ecstatic that after years of toil, he had "made" it.
In fact, he considers it the worst time of his life. His wife had her own career going with much success throughout the '80's, but the sudden success pushed Crowell on the road and put a further strain on their up-and-down marriage.
"It just was not a good time. The making of it, leading up to, it. It just so happened that the after the period that came afterwards was pretty difficult. I wasn't in a position to enjoy what was going on for a lot of different personal reasons."
"Hindsight, I'm definitely okay with it. Had I been really happy and enjoying the moment, I might have gotten self-congratulatory and satisfied and might not be doing the work I'm doing now. I think things always work out."
The marriage "came apart because of the time and energy I was devoting (to my career). But you know what, it would have anyway. That's a good thing because it moved both of us onto other things."
Cash married producer John Leventhal and lives in New York. Crowell married Claudia Church, who had an album out on Warner in 2000, which did little. She also is a model, painter, actress and writer.
Crowell never again reached the level of "Diamonds & Dirt," although he enjoyed other hits with "Many a Long & Lonesome Highway," "If Looks Could Kill "And What Kind of Love."
He switched from Columbia to Tony Brown's MCA for a few albums, 1994's "Let the Picture Paint Itself" and "Jewel of the South" the following year.
Crowell was not too happy with his time there, feeling he made a concerted effort to have a radio hit, which didn't pan out at all.
Next stop was a return cup of coffee with Warner, which resulted in no album released.
"The problem with the record I was making for Warner was that it was the same old thing, making a record for a record company, making sure they have singles, making sure they have marketing tools," says Crowell. "I realized that wasn't what I wanted to say. My heart wasn't into that. (Label head) Jim Ed Norman, being a really good man, let me go off on my own. I realized it was an opportunity for me to do the work I wanted to do that was in my heart instead of walking that schizo line of being an artist and fulfilling someone's commercial needs."
In between his own albums, Crowell also helped form a rock group The Cicadas, which had one record to its credit.
Crowell began working on "The Houston Kid" in 1999 on his own dollar. He had finished music before shopping it around.
He considered a major label.
"I realized that with them, they were going 'we like this music,' but I was realizing that in the corporate world, they were willing to sign me and put my record out based on my track record as opposed to what I had actually done. It wasn't with a passion for what I had done. It was because I have a name. With these Sugar Hill folks, they were laughing and having fun and talking about the music and the songs and actually giving me some input for how to even go farther into independence. I realized this is fun. These guys are having fun. They're not worried about all of the things that a corporate record company does. Quarterly profits were way way down the line, compared to a good piece of work."
"There were other indies I was considering, but then something else happened, which was the Sugar Hill people started showing signs of having more money. Let's be honest here. It's not all altruistic. They had some money to back up their giggles."
Crowell, who is moving back to LA from Nashville, seems satisfied with "The Houston Kid" in having made the album on his own terms.
When asked about his current status, Crowell says, he was "perfectly okay with it. When I was not okay with it, it was when I tried to pander to the commerciality (of the music), and at the end of the day, when nothing really happened on the commercial front, and I was left with a record that wasn't really what I could do as an artist. When you start chasing that radio format, you don't even have your own self-respect. I don't blame it on anybody else. I have to take responsibility for my choices and myself."
"If nobody played it, and nobody bought it, I've made something that I'm proud of it," Crowell says of "The Houston Kid." "To me, that's a bigger success."