Jack Ingram Scores First Top 40 — and Keeps Going

"Wherever You Are" Is Singer's Best Recording Effort Yet

Jack Ingram has chased his recording career on a treadmill. Time after time, the introspective Texan has signed recording contracts only to see his deal or the label itself slip away.

But things are getting better. Lots better. This week, Ingram’s Live: Wherever You Are, his first CD for Big Machine Records, is the highest entry on Billboard’s country albums chart, making its debut at a very healthy No. 33. His first single from the album, “Wherever You Are,” moves up to No. 29 and is still showing momentum. It is his highest-ranking single to date.

A few days before the album came out, Ingram taped a show for Sirius Satellite Radio in front of an audience of Nashville music journalists and Big Machine staffers. Sitting on a high stool and accompanying himself on guitar, Ingram demonstrated that he wasn’t only a gifted singer and songwriter but also a wry and engaging storyteller. By the time he finished his 10-song program, the Houston-born artist had charmed his listeners through the highs and lows of his life — both personal and professional.

Near the end of his set, he reflected on that age-old conflict in the music business between art and commerce, a moral territory he knows better than most. “Being cool’s OK, but it’s not what it’s cracked up to be,” he observed. Then, with a smile, he added, “I want to sell out — every seat, every night.”

Ingram recorded an album he titled Live at Gruene Hall: Happy, Happy in December 2003. Since he had no recording contract at the time, he released it the next year on his own label. When Toby Keith and record promoter Scott Borchetta departed UMG Nashville and launched Show Dog Nashville/Big Machine Records in 2005, they picked up the album. The label deleted some original tracks, added some new ones — including the studio cuts “Wherever You Are” and “All I Can Do” — and, with a new title, made the collection its flagship release.

The album marks a plateau on Ingram’s very long climb toward national recognition. He recorded his first two independent albums — Jack Ingram and Lonesome Question — in 1993 and 1994, not long after he completed his degree in psychology at Southern Methodist University. By the time he graduated, he says, he was already making a living performing his music.

Although he didn’t learn to play the guitar until he was in college — when he taught himself — Ingram was first attracted to performing through his high school drama classes.

“I certainly knew then — a light bulb was turned on,” he tells CMT.com. “I was in a play my senior year, and I knew that was something I really dug and that got me to another place, mentally, that I’d never been to before. … My affinity for songs and music was well into development by that time. I knew that when I put on my headphones and listened to [Willie Nelson’s] Red Headed Stranger that the world stopped.”

Ingram’s first big break in Nashville came in 1996 when he signed with Rising Tide Records, a new imprint with major label backing. Here he released two albums — Live at Adair’s (1996) and Livin’ or Dyin’ (1997). This alliance yielded only one chart single, “Flutter,” which peaked at No. 51. Soon after, Rising Tide went out of business and ebbed into history.

The next Nashville stop for Ingram was Sony Music’s Lucky Dog label, where he made two more promising albums — Hey You (1999) and Electric (2000 but revised in 2002). Again, his chart activity was disappointing. Only one single, “How Many Days,” charted. It topped out at No. 64. Ultimately, Lucky Dog dropped him.

Concurrent with these Music City reverses, however, Ingram continued to build his reputation through incessant performing in Texas and by the emotional intensity of his songs. Even in his headiest days, he still lived in Texas. “I never had a Nashville mailing address,” he says.

In addition to singing, Ingram has also become a radio personality over the last couple of years.

“It just kind of happened,” he says. “I was talking to a DJ friend of mine in Dallas. I told him that I had an idea for a show where I basically took my own CDs up to the station and played whatever I wanted to for an hour. And he bought it. … The idea is like sitting down at a party with one or two of my friends who haven’t heard some of these artists before and turning them on to what I consider to be good music, whether it’s Willie Nelson or Wilco or Bruce Springsteen or Buck Owens.” XM Satellite Radio has since picked up the show.

“I really feel like [country music] has opened up over the last few years,” Ingram muses. “It’s a little more apropos of guys who grew up listening to rock music and George Strait. In my early years — ’96, ’97 — I just thought it was a little shticky, a little campy. Shticky and campy and humorous stuff are all fine and good as long as it’s tempered with the more serious and hardcore stuff that they’re letting on [radio] now.”

Ingram has come to terms — sort of — with the eternal tug between Texas musical independence and Nashville’s supposed conformity.

“I was reading in a magazine that all successful people have to have a nemesis as a means of motivation,” he says. “So maybe that’s it. … Maybe we’re trying to find something to point our arrows at, and Nashville’s an easy target. Aside from that, I think there are different philosophies that go into making and building a career when you come from Texas and when you come at it from the Nashville establishment side of it. It’s just two different architectures of a career. One is a lot more thought out, planned out and mapped out and done by a committee. For better or worse, that’s why people bitch about it being a cookie-cutter system.”

It was only natural, Ingram reasons, that Texas artists have historically resented Nashville, even as they sought out its star-making machinery.

“If you start a career in Texas and you make your way to Nashville, there was no committee,” he notes. “It’s much more a true-life journey for these artists. They had to go out and figure out who they were before they ever had a record deal. Then [they] get into a system that’s built around, ’Well, this is the way we’re going to do it because it worked the last time and it worked the time before that. You need to get on board.’ It’s just an immediate friction that some people can’t work through. And it’s hard to work through that. These are just the natural things that happen. I feel like I’m aware of them. I may have rebelliously or flippantly said things just to make a point or whatever. But, man, I’ve always understood that I’m not going to have this career without Nashville.”

Recently, Ingram was able to savor one of the things that Nashville could do for him when he heard “Wherever You Are” played on American Country Countdown. Hearing one of his songs on the syndicated radio series had been a dream, he says, ever since he began listening to the program on his long drives across Texas.

“A radio DJ friend of mine in San Diego sent me [a copy of the show] the first week, when it was No. 40,” Ingram says. “And it was great, man. It was really cool.” Here he switches to his “radio voice” and intones, “Making his debut on the Top 40 — Jack Ingram.”

Edward Morris is a veteran of country music journalism. He lives in Nashville, Tennessee, and is a frequent contributor to CMT.com.