And in the fickle music world, that meant he left Asylum, hunting for a new label.
That's not the only new part about "Desire Road." While "Dreams & Saturday Night" has a more twangy sound, "Desire Road" incorporates elements of pop and soul into the country mix.
"I feel when I made this record, I wasn't trying to think too much (about what) I needed to do or what's expected of me in terms of country radio," Woodruff says from Nashville. "We just kind of let the songs sort of find their own way. I enjoy the record. I feel it's a bit more rocking than my first record. On the other hand, I think it's more commercial than the first record. It's more acceptable."
"Those songs really work in the context of a country album. I guess what I'm most proud of is we developed our own sound on this record. The way in which steel guitar works with 12-string guitar, more of a Byrdsy feel," he says.
"Dreams & Saturday Nights," released in March 1994, resulted in three singles being released, but the highest charter - "Hard Liquor, Cold Women, Warm Beer" - only reached 68 on the charts, according to Woodruff.
With hat act music abounding, Woodruff's was not the kind of country music being played on the airwaves, even if he did receive video play.
Woodruff, 36, harbors no ill will towards Asylum, his first label. "When I started out with Asylum, it felt like the right place to be. I was the poster boy. My first record fit in with their (plans) completely - the idea of creating a singer/songwriter label. Historically, Asylum has been a record label that's embraced singer/songwriters who might be a little left of center."
"Towards the end of my record, everybody was disappointed that we didn't chart some songs on country radio," Woodruff says. "In a way, perhaps they might have been a ahead of their time. "
Woodruff knew he had to make a change. He sat down with label head Kyle Lehning. "He felt that we could have another go at it (second album), but I think the bloom was off the rose," Woodruff says.
"He was encouraging me to go more mainstream, and I felt like I didn't really want to do that," says Woodruff, a New York native. "My instincts were just telling me we had a good shot with this record. They believed in it. I believed in it. It must be time to make a change."
By the summer of 1994, Woodruff asked for his release. "I wasn't mad," he says. "They don't owe me a living. They know I did my best."
"I'm happy because they got my foot in the door," Woodruff says. "They gave me a shot."
Woodruff, who moved to Nashville from New York six years ago, took a break and started writing songs. His manager had a short list of record company people he might want to work with. Roy Wunsch, a founder of the new Imprint label, who had been at Sony, was at the top. "They were very familiar with my history and what happened with Asylum. It just felt really good."
Imprint signed Woodruff as its first artist in 1995 even before the label had offices. "It was really a commitment based on people, not so much on the record label," Woodruff says.
The label has since signed the likes of Al Anderson and Gretchen Peters, both known for their songwriting.
Besides a different label, Woodruff opted for a new producer, Ray Kennedy, instead of Steve Fishell, who oversaw his debut. Woodruff says he would have hooked up again with Fishell, but saw a conflict of interest because Fishell's wife has a key post at Imprint.
Woodruff says he thinks Kennedy is responsible for the change in sound on "Desire Road." "We kind of let the pop side of me out a little bit on this record," Woodruff says. A reference point is "I'm Losing You" with echoes of The Beatles.
"He looked at the songs that I had and gravitated to songs that some people in Nashville making a country record might not want to include," Woodruff says. "He didn't let songs like 'I'm Losing You' and 'I Want You' scare him. He thought those were some of the best songs written at the time, and I cut them."
Woodruff acknowledges the label's interest in seeing him get radio airplay led to recording a few covers. The lead-off is John Fogerty's "Almost Saturday Night," a bouncy romper.
"It's a song I've been wanting to do for awhile," Woodruff says. "In the process of recording the record, there were some pressure from the record label to come up with a 'radio song.' They were pleased with the direction we had taken. They had some songs we thought that might be right for radio, but they weren't really sure. I kind of dug into my album collection and thought about songs I'd think of doing for a few years. It popped up. It did what we wanted. It was a really fun song to record and to produce. It helped us kind of turn the corner on the project...When we came up with that song, it may not be a typical country radio song, but it's undeniably commercial."