Songland's Shane McAnally Shares Stories Behind His Biggest Hits with Blake, Kacey & More

Over the past decade, Shane McAnally has become the go-to songwriter in Nashville thanks to his penchant for a perfect hook or turn-of-phrase.

He’s earned a reputation behind the scenes as a hitmaker, crafting more than 40 No. 1 hits. But now McAnally is in the spotlight thanks to the NBC reality competition Songland (Mondays, 10 p.m. ET), on which he is a mentor alongside OneRepublic frontman Ryan Tedder and Ester Dean. And McAnally is giving fans a peek behind the curtain and opening up about his songwriting process on his new Instagram Live video series, “Behind the Hit.”

RELATED: How Songland’s Shane McAnally Went from Homeless to Country's Hottest Hitmaker

The Grammy winner recently opened up to PEOPLE about some of the most meaningful tracks he’s written over the years.

“It's hard to forget how a song was written when it's special because you usually had something happen that you're like, ‘I'll remember this,’” McAnally, 45, says. “And that usually is the indication that the song is going to have a life beyond just being in the room.”

“Last Call,” Lee Ann Womack

It didn’t reach No. 1, but Lee Ann Womack’s “Last Call” is one of the most important tunes McAnally’s written because it’s the first cut he sold as a professional songwriter. The track began with a different title, though.

“You start with an idea, and you're so stuck on that idea that as the hook evolves, you still can't think of it as anything else. We kept singing, ‘I bet you're in a bar, listening to a cheating song,’ and then ultimately the payoff was, ‘I bet you're in a bar because I'm always your last call,’” he recalls. “We pitched it with the title ‘I Bet You're in a Bar’ to Lee Ann Womack because we didn't have that 'last call' piece for most of the day. Then they came back and said, ‘Yeah, but we think it should be called 'Last Call.' And that made a whole lot more sense.”

Based in Los Angeles at the time, McAnally relocated as soon as he sold the song: “I packed my stuff up and moved to Nashville, all based on this song that we didn't even know what it was going to be,” he says. “Then her performance of it went on to get nominated for a Grammy. It really changed things for me. It was a first step.”

“Somewhere With You,” Kenny Chesney

McAnally’s career took off after his first cut with Womack. A year later, Kenny Chesney released “Somewhere With You,” which became McAnally’s first No. 1 hit.

“Kenny was the most influential record-maker on the radio. He was the one everybody wanted to get their songs recorded by,” he says. “When that happened, everything sort of took off.”

“Mama’s Broken Heart,” Miranda Lambert

McAnally calls Miranda Lambert’s No. 1, “Mama’s Broken Heart,” “the most true-to-life song that's ever been a hit for me.”

The song was inspired by his relationship with his mother and sister, he says: “My mom was a single mom, so the three of us were sort of a pack. Even as adults I'd be on the phone with my mom and then hang up and be on the phone with my sister, and they're talking about my sister, like, cutting her hair and being nuts over a breakup. And my mom would be like, ‘I can't listen to it anymore.’”

McAnally went on to co-write the song with his friends Kacey Musgraves and Brandy Clark.

“I started telling them the story of my mom and my sister. And they both had their own versions of that story with their mom,” he says. “I had told Brandy Clark that I wanted to write a song like ‘This Ain't Your Mama's Saturday Night’ or ‘This Ain't Your Mama's House Party’ or whatever. And Brandy said, what if this is that song that you've been talking about, ‘This Ain't Your Mama's Broken Heart’? And that's how that song started.”

“Merry Go ’Round,” Kacey Musgraves

McAnally and Musgraves have developed a strong bond over the years and written several albums-worth of songs together—and his children were even in her wedding! Musgraves’s “Merry Go ’Round” was their first hit together.

“‘Merry Go ’Round’ is the song that it feels like a metaphor for our relationship and the kind of songs we made from the beginning — and the fact that we both came from small towns,” he says of the track, which they worked on with fellow songwriter Josh Osborne.

McAnally’s mother also gave them an idea for this track about small-town life.

On a visit to her home in Texas, “we were talking about the people that live next door to us, and they had these cars and all are in the driveway and in the front yard,” McAnally recalls. “Josh asked my mom, ‘What are all those cars doing next door?’ And my mom said, ‘I don't know, Josh. They're selling Mary Kay or Mary Jane or something.’ And that was the light bulb moment that happens for songwriters.”

The track became the lead single off of Musgraves’s debut album, Same Trailer Different Park — and it still occupies a special place in McAnally’s heart.

“When my husband [Michael Baum] and I got married, Kacey sang at our wedding,” he says, “and that was the week that ‘Merry Go ’Round’ went to radio.”

“Nobody But You,” Blake Shelton & Gwen Stefani

Last year, McAnally — who had already written songs for Blake Shelton — was in a writing session with Gwen Stefani.

“One of the main things we talked about was her and Blake, and she just was telling me how happy they were and how glad they were they found each other at this part of their life and they're just truly in love,” he says.

The Voice coaches' love story inspired McAnally to write a song about them with co-writers Osborne, Ross Copperman and Tommy Lee James. They pitched it to Shelton’s label but never heard back. So, months later, when McAnally was promoting Songland during The Voice, he told Shelton about it.

“He said, ‘Send it to me’ and was walking away, and thank God I said this — it was scary but I asked, ‘How do I send it to you?’” McAnally recalls of the impromptu pitch, which happened during a commercial break. “[Producers] were like, ‘Blake, you have 10 seconds.’ And he goes ‘Send it to Gwen.’ And again, this is one of the scariest things ever is you don't know if someone's just being nice … But I sent it to Gwen and I said, ‘This is going to sound crazy, but Blake just told me to send this to you because I don't have his number, and so here's the song.’”

RELATED VIDEO: Blake Shelton and Gwen Stefani Drop 'Nobody But You' Music Video Days Before Grammys Performance

Blake Shelton and Gwen Stefani Drop 'Nobody But You' Music Video Days Before Grammys Performance

The video features several clips of the couple singing while cuddled up on the couch with their dog Betty

McAnally waited for months with no response — “and then of course, Blake and Gwen called me on FaceTime and were like, ‘Can we cut this song?’” he says. “I was like, ‘Good Lord, y'all made this like a movie or something, leaving me on a cliff!’”

Shelton and Stefani released the duet last year.

“I never had a song that has been so propped up by the artists ever,” McAnally says. “They have put their whole heart and soul into promoting this song and performed it everywhere. And it's connecting because people see that it's real. It is very gratifying to watch them take that song as their own, because you really wouldn't know they didn't write it. And that's the whole point of interpretation is to take the song and make it yours, and that's what they've done. And I couldn't ask for anything more.”