The one contestant who made it easy on him? Bria Kelly, who at just 18 managed to nail the Rolling Stones classic "Wild Horses" with a performance so polished it could rival seasoned singers twice her age.
"I've stolen everyone that you sang against," declared coach Blake Shelton. "Looking back, maybe that's because you made people step up."
Adam Levine expressed relief that the Virginia-based singer, who prompted a four-chair turn in the blind auditions, was strong again after a shakier battle round.
"I was worried about you last time, like you weren't you for a second," Levine said. "I'm really pleased to say that you're back. And thank God because you're one of my favorites."
At the end of the show, Usher announced her name first to move on to the live shows, and made it clear keeping her was a no-brainer.
"This artist was obviously a shining star from the moment I heard them sing," he said before revealing his choice. "Not only have they taken what I had to show them about themselves but grown more confident as a vocalist."
The other singers didn't make Usher's choice quite so easy.
T.J. Wilkins, a soulful singer trying to further his music career so he can escape life in South Central Los Angeles, kicked things off with an energetic version of "Tell Me Something Good." that had his coach grinning.
"You just reminded us of the careless, free nature of that period of time and what that music was," Usher said. "You just killed it."
Melissa "MJ" Jiménez sang next, and took a risk choosing a stripped-down version of Beyoncé's "Halo."
"I think there were moments that were really beautiful and moments that there was some trouble," Levine told her. "But it was a courageous move and it was good."
Stevie Jo, a Texas R&B singer with heavy metal roots, prowled around the stage while singing "The Thrill Is Gone" by B.B. King in a performance that seemed to win over the coaches.
"I love watching Stevie Jo perform," Shelton said. "It's like he's sneaking up on a rabbit the whole time. I can say that because you nailed the singing part. I know you're the real deal. I'm a fan."
Usher seemed pleased too, and praised his ability to connect with the heartache in the song.
"I am a fan of yours and your growth and also a fan of how courageous you are as a vocalist," he said.
Another courageous vocalist? Josh Kaufman, an Indiana father of three who closed out the night with "It Will Rain" by Bruno Mars. Kaufman, a steal from Team Adam in the last battle round, didn't seem nervous on his Team Usher debut, and his emotional rendition resonated with the coaches.
"They should remove the dagger from my heart," Levine said. "I'm so relieved and happy you're still in this because you deserve to be ... I hope you make it to the top."
Usher told him, "You really did an incredible job of making it almost impossible to make a decision."
But making a decision was required. After Usher announced Kelly's name as his first artist moving on to the live shows, he revealed he would also advance Kaufman.
That left Jiménez, Stevie Jo and Wilkins vying for the last spot. In a bit of a surprise, he chose Wilkins to move on, forcing the highly praised Stevie Jo and Jiménez to say goodbye.
The live shows kick off Monday (8 p.m. ET) on NBC.