Ask A Music Critic: What Is The Best ‘Greatest Hits’ Album Of All Time?

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Welcome to another installment of Ask A Music Critic! And thanks to everyone who has sent me questions. Please keep them coming at

I just started your book Twilight Of The Gods (plug, plug, plug) and your mention of greatest hits albums having a lower rank on your tape shelf as a kid inspired this question: Are there any greatest hits albums that deserve respect?

I think there are two categories that do: Greatest hits albums that have cultural cache as an entity itself, like Bob Marley’s Legend, which has taken on a life of its own as a dorm room essential; and greatest hits albums that have higher aspirations than just collecting the hits, like Neil Young’s Decade, which tells the story of his career up to that point with deep cuts, unreleased tracks and, of course, really cool cover art.

And there’s the potential third category: Greatest hits albums that have every song you need. I’d put Steve Miller Band’s Greatest Hits 1974-1978 here. Thoughts? — John from Malden, Mass.

What a timely question! This week, it was reported that the Eagles’ Their Greatest Hits, 1971-1975 surpassed Michael Jackson’s Thriller as the best-selling album ever. In an era in which album sales continue to drop exponentially, the “best-selling” distinction feels a little antiquated. (Jackson has far out-streamed the Eagles on Spotify.) Nevertheless, the quintessential pop album of the ’80s is presently playing second fiddle to a compilation that the band members themselves objected to at the time. The Eagles were still a working band when Their Greatest Hits was released in 1976. (It came out less than a year before Hotel California, the Eagles’ most popular studio album and currently no. 3 on the all-time best-selling albums list. Sweet Jesus, people love them some Eagles!)

Since you’re the one who mentioned my book — available at fine booksellers and online everywhere! — I do write about how when I was a kid my taste was informed by reading music criticism, and one of the earliest lessons I gleaned was that greatest hits albums were not “real” albums. If you wanted to be a “true” fan, you had to dig into the proper studio output in order to ascertain an artist’s “essence.” Or something like that.

Now that I’m older and slightly wiser, I’ve grown out of that adolescent snobbiness. I still prefer proper (or artist-sanctioned) albums over (record label-sanctioned) compilations, but I’m also fascinated by the idea of greatest “greatest hits” albums. Not playlists, not boxed sets — traditional greatest hits collections that are packaged to look like regular albums, and sometimes take on the stature of regular classic albums.

I have got to hand it to you, John: Your three categories for greatness in the field of greatest hits albums make a lot of sense to me. Adding to what you’ve already mentioned: ABBA’s Gold, like Legend, seems like the perfect example of the first category, though you could also make a case for it belonging in the second and third categories. America’s Greatest Hits – History is a little less celebrated than those two records, but I would slot it for sure in the first and third categories, and possibly even the second. Gold and History do a great job of detailing career narratives for their respective artists, adding up to what feels like definitive takes.

I’ve often said that the 1993 Greatest Hits album for Tom Petty And The Heartbreakers — the one with the garish red cover — is my favorite greatest hits album ever. It’s certainly one of the greatest “road trip” records of all time. (It also scores extra points for introducing “Mary Jane’s Last Dance,” which the band recorded as a bonus track, and then it became an actual greatest hit.) It probably belongs in the first category, though I wonder if the third category actively disqualifies it. (It most definitely does not include all of the Tom Petty tracks that you need.)

The third category is the thorniest one here, because it’s arguably the most important (providing “every song you need” is a greatest hits album’s number one job!) while also being the hardest to satisfy if you bother digging deeper into an artist’s discography. Madonna’s The Immaculate Collection and Credence Clearwater Revival’s Chronicle are both classic greatest hits albums — put them in the first category — but both acts also have several great studio albums worth investigating. Ditto that for the original Greatest Hits by Simon & Garfunkel, a staple of every baby-boomer parent’s record collection. (It’s the one where Paul and Art look like Muppets on the cover.) You get all the biggest chart hits on that record, but you won’t get “The Only Living Boy In New York.”

As always with music, the more you listen, the more you need.

Who is the “better artist”:

— The one who releases only three albums, all of which are great, and then calls it quits.
— The one who has 25 years of consistently above average music, without many peaks or valleys in quality.
— The one who for 25 years has some really high-quality peaks, but also some embarrassing lows.

Thanks! — Eric from Lexington, KY

I think about this question a lot, Eric. Are you spying on me? Do I need to contact the authorities? For the sake of this column, I’m going to trust you and assume that you’re not stalking me.

Now, let’s walk through your three scenarios. This is how I would rank your theoretical artists, based on my own personal interest.

3. The one who has 25 years of consistently above average music, without many peaks or valleys in quality.

You’ve just described a lot of bands I adore: Spoon, Yo La Tengo, Belle & Sebastian, Built To Spill, Sonic Youth, even R.E.M. (Around The Sun is no masterpiece but for a career nadir it’s pretty good.) But, generally speaking, a really consistent catalogue is like a really reliable car — you love it, you can count it, but you don’t really ever think about it. That’s the whole point of a reliable car, to be this stress-free convenience that you don’t have to think about.

2. The one who releases only three albums, all of which are great, and then calls it quits.

The upside of this category is mythology — if you’re Jimi Hendrix, Nick Drake, Kurt Cobain, or the Notorious B.I.G., there was never a time when you weren’t awesome in the public sphere. So everything you ever uttered is infused after the fact with romance, profundity, tragedy, and extreme historical significance.

The downside of this category is that there just isn’t a whole lot of music to dig through. Everybody loves Nirvana, but when was the last time you actually listened to them? As wonderful as Nevermind is, do you ever need to play it again? Is it even possible to actually hear that album and get past all of that romance, profundity, tragedy, and extreme historical significance?

Still, you can’t beat mythology, which is why I tend to obsess over artists in the class a little more than the “reliable car” acts.

1. The one who for 25 years has some really high quality peaks, but also some embarrassing lows.

This is my favorite kind of artist by far. Dylan, Prince, Bowie, Neil Young, Kanye West — all of the most fascinating icons put out stupefying masterpieces and even more stupefying disasters. That’s what happens when you take big swings every time you step up to the plate. Sometimes you produce Blonde On Blonde or 1999 or Yeezus, and other times you come up with Knocked Out Loaded or
Lotusflow3rMPLSound or Ye. But for this class of artist, even the failures are fascinating, and often essential. This isn’t a reliable car. This is a sports car that goes from 0 to 100, or straight off of a cliff. What more do you want out of life?

Sometimes I feel like your album reviews come off a little harsh. (Admittedly, maybe I’m just soft.) But it made me wonder: How many musicians fucking hate you? — Eddie from Hoboken

Very good question, Eddie. Most of my interactions with musicians are extremely cordial, though I generally only meet artists who I already admire. The ones I have panned have, to their credit, taken their lumps in silence and cursed my name in private.

I honestly hope my reviews aren’t that harsh, though. Sometimes, honesty requires me to be less-than-nice, because ultimately I write for listeners, not the artists. I would never deign to give an artist “feedback” on their work. I’m writing for people who love music and want an opinion on whether an album is any good. So, those are the people I have to keep in mind.

But I do respect and empathize with musicians who are put under the critical microscope. I have been reviewed myself, sometimes unfavorably, and it makes you feel really vulnerable. You spend a long time making something that feels personal, and you put it out in the world to be judged — and that’s pretty terrifying! Rarely does anybody in your regular life tell you exactly how they feel about you in unsparing language. And yet that’s what critics do on a regular basis. The job requires you to be unsparing, but it’s good to have some empathy for your subjects, and respect for the courage it takes to put yourself out there.