Distilling a career as long and legendary as Willie Nelson’s into just 16 songs demands limits. This set features his No. 1 hits on the country charts between 1975’s “Blue Eyes Crying in the Rain” and 1989’s “Nothing I Can Do About It Now.” A few big hits (No. 2s, mostly) from the era are bypassed for smaller hits such as 1977’s No. 4 country hit “Uncloudy Day” and 1980’s No. 6 country version of Gregg Allman’s “Midnight Rider,” but the set covers most of the time period. Other obvious highlights here—such as “Georgia on My Mind,” “On the Road Again,” “Always on My Mind,” and “Angel Flying Too Close to the Ground”—are among Nelson’s most career-defining. Naturally, a larger collection would encompass more of Nelson’s career and uncover lesser-known gems. But for what 16 Biggest Hits sets out to do, it does so enjoyably, playing like one smooth album that just so happens to include an unusual amount of famous songs.