Tippin switched to Lyric Street Records in 1998, where he recorded four more studio albums, counting a compilation of Christmas music. In the wake of the September 11, 2001 attacks, he released the patriotic anthem "Where the Stars and Stripes and the Eagle Fly"; although it was his most successful crossover single, he saw his popularity decline a second time after its release. After parting ways with Lyric Street in 2006, he founded a personal label known as Nippit Records, on which he issued the compilation album Now & Then. A concept album, In Overdrive, was released in 2009.
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