The Best of Bob Dylan (2005)
1. Blowin' in the Wind
2. The Times They Are A-Changin'
3. Mr. Tambourine Man
4. Like a Rolling Stone
5. Rainy Day Women #12 & 35
6. All Along the Watchtower
7. Lay Lady Lay
8. Knockin' on Heaven's Door
9. Tangled Up in Blue
10.Hurricane
11.Forever Young
12.Gotta Serve Someboy
13.Jokerman
14.Not Dark Yet
15.Things Have Changed
16.Summer Days
 
As far as retrospective compilations go, The Best of Bob Dylan attempts the impossible—and proves it. The notion of distilling a career as sprawling, contradictory, and epoch-defining as Bob Dylan’s into a single disc was always bound to falter. In fact, it had already been tested, and found wanting, with the earlier Essential Bob Dylan—a two-disc set that many argued was itself too cramped to do justice to the catalog. To halve that again borders on the absurd.
What emerges, predictably, is a skeletal overview: a sequence of canonical titles arranged not with thematic or tonal intent, but seemingly under the weight of obligation. Yes, the songs themselves are unimpeachable—Like a Rolling Stone,Tangled Up in Blue, Blowin’ in the Wind, among others—but context matters. Torn from their albums, and stripped of the cultural and musical atmospheres that gave them their resonance, they risk becoming postcards from a journey far too vast to be condensed.
More troubling, perhaps, is the compilation’s failure to offer anything distinct. It does not illuminate lesser-known corners of the discography, nor does it reframe familiar material in a new light. It simply exists—curated more for convenience than discovery. For the uninitiated, it may serve as an entry point. But for anyone even passingly familiar with Dylan’s work, it feels inert, like a coffee-table book of fragments.
It is telling that, only a few years later, Dylan’s camp would reverse direction entirely with the Triple CD Dylan set—a far more ambitious collection that sought to confront, rather than evade, the problem of scope. That release, while imperfect, at least acknowledged the immensity of the task. This one skirts it.
There are, undeniably, finer compilations available—ones that explore, challenge, or at least adequately survey Dylan’s phases and contradictions. The Best of Bob Dylan is not among them. It is neither essential nor particularly insightful. It is a placeholder.
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