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He’s written smashes for nearly everyone on country’s current A-list — Kenny Chesney, Luke Bryan, Lady Antebellum, Miranda Lambert, Keith Urban, Kelly Clarkson, The Band Perry — but Nashville powerhouse Shane McAnally’s rise to the top didn’t exactly follow the most direct route.

The native Texan, now 39, began as a recording artist himself, and only returned to Music City in late 2007 after an almost eight year break from the business. It took Chesney taking a chance on his “Somewhere With You,” which hit No. 1 on the country charts in 2008, to take him from songwriter non grata to one of the industry’s most in-demand scribes.

“All of a sudden, everything I had been writing mattered,” McAnally tells EW in a feature in this week’s print edition. “He sort of anointed me, not even knowing he did it.”

Five years later, McAnally is writing for the best of the best in country music full-time. He even competed against himself for Song of the Year at this year’s CMA Awards for co-writing “Mama’s Broken Heart” for Lambert and “Merry Go Round” for Best New Artist winner Kacey Musgraves (whose debut album Same Trailer Different Park he also produced).

The night before the CMA ceremony, EW sat down with the hit-maker backstage at his CMA Songwriters Series show at the Country Music Hall of Fame and Museum, where he held a silver-haired auditorium rapt with the stories behind his biggest hits. Once he stepped offstage, we asked him to tell a few more stories about his life, which you can read in the magazine in full. Here are a few notable bits:

On his fortuitous start: “I came up here on spring break with a couple of guys I went to school with,” McAnally, who left the University of Texas when he was 19, remembers. “We were in my grandmother’s minivan, and we went to the Bluebird [Café]. I’d heard that you could go in and put your name in a hat, and if they drew your name, you got to play a song. And that’s what I did. And they drew my name. I mean, it sounds so made up, but that is really what I did. I [moved to Nashville] probably two months after that.”

On being out in Nashville: “It feels unprogressive, the attention put on that,” McAnally, who married his longtime partner Michael Baum in 2012, says. “I think people don’t give Nashville enough credit in that regard, I really don’t. I just have not seen the separation here.”

On country music’s glut of tailgate songs: “I mean, we’ve all written them. Sometimes you just want to write a party song. [Other people’s] just seem to get cut more. I think they, at times, can even get frustrated with it. They have stacks of songs that could compare to the greatest. Those don’t always get the attention. We’re trying to make a living and some days it’s just fun to write those songs. Why do those always get cut? Who knows? That’s not been my story. I mean, I’ve had a few party songs get cut, but maybe it just doesn’t read as authentic on me.”

Below, enjoy some of McAnally’s greatest hits — including two of the buzziest tracks in country music this year: “Follow Your Arrow” by Musgraves and “Songs About Trucks” by Wade Bowen, a song that’s being heralded as the ultimate anti-truck antidote, which McAnally penned with Brandy Clark.