While it has its fair share of big hits and great songs, RCA/Legacy's 2005 release 16 Biggest Hits doesn't necessarily contain all of Waylon's biggest hit singles. For one thing, his 1968 smash "Only Daddy That'll Walk the Line" is nowhere to be found, nor are such iconic country Top Ten hits as "The Chokin' Kind," "You Ask Me To," "Bob Wills Is Still the King," and "Dreaming My Dreams With You," and all are missed. That said, all of the 16 songs that are here -- with the exception of the OK closer, "Drinkin' and Dreamin'," a cut from 1985 that's not all that distinctive -- are very good to excellent. Any album that contains "I'm a Ramblin' Man," "Are You Sure Hank Done It This Way," "Good Hearted Woman," "The Wurlitzer Prize (I Don't Want to Get Over You)," and "I Ain't Living Long Like This" is a good listen, after all. There are other compilations that are better career overviews, but this is still a respectable, enjoyable sampler of Jennings' classic work.
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AllMusic Review by Stephen Thomas Erlewine