The singer visited the show to promote his new album, Texoma Shore, but things got a little awkward when he and Jimmy started to play, "Name That Song."
The house band, The Roots, played instrumental versions of popular songs as The Voice judge and late night host raced to guess the name of the tune.
However, when the band started to play "Hollaback Girl," one of Gwen's biggest hits, the 41-year-old country star stood there cluelessly.
"What's that?" he asked.
"All I know is that Blake is in a lot of trouble right now," Jimmy laughed as he realized what song it was.
Blake, embarrassed and defeated, then sat down on the stage. "I came to this show to promote my album and I am losing everything in my life!" he exclaimed.
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