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Songland Recap: Macklemore Brings Winning Song to Lollapalooza in Brazil

This was a tough decision!

Written by Tammy Ragusa
Songland Recap: Macklemore Brings Winning Song to Lollapalooza in Brazil
SONGLAND -- "Macklemore" -- Pictured: (l-r) Shane McAnally, Macklemore, Iro -- (Photo by: Trae Patton/NBC)

After a brief hiatus, Ester Dean, Shane McAnally and Ryan Tedder are back to work with three new songwriters on NBC’s Songland.

As we have learned since the show started earlier this year, four songwriters took their turn to perform an original tune for the three coaches and a special guest each evening who would go on to record the winning songwriter’s song. On this night, the aspiring writers were excited to sing their creations for singer-songwriter Macklemore.

Before the writers stepped up to the mic, Macklemore explained that he had was approaching this with an open mind. “I’m open to whatever type of song it is,” he said. “It could be an emotional song, it could be a fun song. What I’m looking for is something that inspires me. Something that pushes me creatively.”

First up was professional busker Iro from Brooklyn, New York with his song, “Shadow.” The pros gave Iro positive feedback, especially on the structure of the song with Ryan comparing it to a Celtic tune. After minimal discussion and Iro’s approval, Ester and Ryan had given the song a slightly different tempo and chorus change, and the overall consensus was that Iro had a contender.

Following Iro were a pair of songwriters from Kansas City, Missouri known as Pop Culture. Their original song, “City Kids,” was primarily a musical arrangement with a “la-la” chorus. Their intention was for a featured vocalist to rap or sing over it. The toe-tapping tune was enthusiastically received by Ryan, who called it the “Slacker Anthem,” but Macklemore also enjoyed the triumphant and “inspiring” vibe. “I love music that makes me feel something when there aren’t even words,” he said.

The third writer to present his original music was Chris Jobe from Dayton, Ohio. His song, “It Could Have Been You,” seemed especially poignant since it addressed the issue of gun violence. It bears mentioning that the song was written and this episode was filmed before the tragic shootings in Dayton and El Paso. The pros complimented Chris’ melody and lyrics, but struggled with the production of the song. “If you’re going to talk about it, it needs to be as kind as possible because somebody could be going through that right now. So, you’re speaking too loud in a room that you don’t know who’s in it,” Ester said.

The final budding writer to perform for the pros was Casey Cook of North Kingstown, Rhode Island singing “Judgments.” Macklemore loved the lyric and the vocal, but wasn’t a fan of the production, so after Casey sang it with just piano, Shane commented, “That’s a different game, right there.” The coaches felt the song was relatable and all were excited about its potential.

After Macklemore gave the songs some more consideration, he chose Pop Culture, Iro and Casey to continue on in the competition.

Following brainstorming sessions with the professionals that they were paired with, each writer or writing team returned to the stage to perform their revised song. And while Macklemore had difficulty narrowing down the original four to three, the decision on whose song he would ultimately record was nearly impossible as each earned rave reviews from the entire coaching panel.

“My decision is harder than I would have anticipated,” Macklemore said after the final performance. But when it came time to choose, he picked Iro’s “Shadow,” insisting the writer not only record the song with him but also perform it with him at Lollapalooza in Brazil.

All of the songs written for the August 14 episode of Songland are now available on streaming services.