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The 11 Greatest Hits From “Greatest Hits” Compilations

It's one of the strangest pop microcosms in history: singles released exclusively from Greatest Hits compilations. We rounded 'em up and ranked 'em to find out what is truly the greatest Greatest Hit of all.

11. The Cranberries – “Stars” (Stars: The Best of 1992-2002, 2002)

The Cranberries are one of those bands where people actually know more songs from them than they’d expect. Their greatest hits compilation opens up with that trifecta of radio staples: “Dreams”, “Linger”, and “Zombie”. While a listen through of the group’s latter-day tracks showcases some unchampioned wonders (the sinewy rocker “Promises” comes to mind), the straightforward MOR romance number “Stars” was truly their hit that never was, a MOR pop number with a chorus that consists of Dolores O’Riordan simply declaring that she loves you “just the way you are”. There’s not much flash or studio trickery to this song: it’s just a straight-ahead guitar pop number, but that confident melody and infectious hook actually make the tune land with some of their best-ever singles. The other “unreleased” number from this set, “New New York”, was a boneheaded 9/11 tribute that didn’t need to happen, leaving what may very well be their last truly great song. (Let’s be honest, as enjoyable as 2012’s Roses was, not a single track on there left us with the same warm afterglow that “Stars” does).

10. Pink – “Raise Your Glass/Fuckin’ Perfect” (Greatest Hits… So Far!!!, 2010)

The quality of each individual Pink/P!nk album is up for debate; some love the Tim Armstrong-produced rock of Try This, while others may prefer the Linda Perry-assisted confessional pop of Missundaztood. There is one thing, however, that is not up for debate: boy howdy does she know how to do pull off a great pop single. Part of the reason why this list included 11 songs instead of 10 was because of Pink, because her own Greatest Hits set included not one but two major singles, and, what do you know: the jittery empowerment-pop confection that is “Raise Your Glass” and the surprisingly potent anthem “Fuckin’ Perfect” went to number one and two on the Billboard Hot 100, respectively.

This is an astounding accomplishment, but one that only speaks to Pink’s undeniable ability at crafting memorable pop hooks. While this is the most recent entry on this list, these two songs came to further embody what everyone has loved about Pink all along. Each track is imbued with her signature style and attitude; for that reason alone, the two new songs from her Greatest Hits album became two of her own Greatest Hits in the process. Few artists will ever pull off that feat once, much less twice in a row.

9. Foo Fighters – “Wheels” (Greatest Hits, 2009)

While there is a large contingent of both fans and critics that will always circle around the Foo Fighters’ first few albums and guard them like hawks, their latter-day albums have proven to be amazingly divisive. Critics ended up loving 2014’s Sonic Highways way more than fans did, just as fans readily embraced the all-rock, no-nuance surge of energy that is 2007’s Echoes, Silence, Patience, and Grace. Yet for a group who can crank out modern-rock chart-toppers with astounding regularity, the new song included on their 2009 Greatest Hits set is a mid-tempo burner, the detail of that main riff luring you in while that slight pickup guitar squeal right at the top of every bar ends up giving just that right amount of attitude and flair to a track that could easily be reinterpreted as a country song under the right circumstances.

This marks the Foo Fighters’ aiming right for the heartland, but the warm, inviting chorus not only proved to be one of the most inspiring singles the band had ever churned out, but one of their most accessible as well. A rock-radio staple that never fully crossed over to the mainstream, this cut may very well be one of the best songs that Grohl and company have ever laid to tape, proving that Foo Fighters will always maintain their unshakable reputation even when they decide to go full-bore pop on us.

8. 2Pac – “Changes” (Greatest Hits, 1998)

A lot of people forget that despite his street-poet reputation, Tupac was absolutely unafraid to go pop when he needed to, and did so without losing an ounce of his credibility in the process. Sure, “California Love” is an easy track to point to as an example of him making his sound a bit more radio-friendly (which worked, becoming one of his two chart-toppers), but when “Changes” dropped in 1998 as a way to promote his Greatest Hits set, some found it way too upbeat, its interpolation with Bruce Hornsby’s “The Way It Is” causing some to think the label was selling out Shakur posthumously.

What makes the song work, however, are the lyrics, which chronicle multiple social issues, some surprisingly potent even to this day. (Case in point: “We ain’t ready to see a black President, uhh / It ain’t a secret don’t conceal the fact / The penitentiary’s packed, and it’s filled with blacks / But some things will never change.”) The song became a Top 40 hit in its own right and, like All Eyez On Me, Tupac’s Greatest Hits became his second album to go Diamond (ten million copies sold). “Changes” actually helped break Tupac out to a wider audience than most people would have ever thought possible. It’s a shame that we can’t celebrate the rest of his posthumous releases with the same fervor.

7. Lenny Kravitz – “Again” (Greatest Hits, 2000)

Lenny Kravitz’s Greatest Hits is his single best-selling release ever, and for good reason: despite what you hear people say, he’s never released a truly iconic album. Singles? That’s another gambit altogether, but Greatest Hits is Kravitz at his most accessible and digestible, his tendency for drawn-out ballads being cut from the equation almost wholesale. Instead, the collection plays to his strengths as a rocker, which, let’s be honest, is the only reason anyone listens to Lenny Kravitz in the first place. If you were alive in 2000 and had a radio and/or VH1, you know full well that this goddamn song was everywhere, a mid-tempo number that is classic in construction and undeniable in its delivery.

“Again” is a romantic rocker with a simple sentiment, but it connected in a way that he hadn’t been able to for years. Sure, it got overplayed to death upon release, but it also became one of Kravitz’s signature songs outside of “Are You Gonna Go My Way?” Again, the hallmark of a great Greatest Hits single is one that doesn’t merely become a hit on its own, but also becomes one of the undeniable “Greatest” in an artist’s discography. With “Again”, Kravitz accomplished that hat trick effortlessly, and, tellingly, never even remotely came close to matching that song’s success since. (Don’t worry though, Lenny: you appear again as a co-songwriter on our number four entry…)

6. Kenny Rogers – “Lady” (Greatest Hits, 1980)

Wait a second, this was off a Greatest Hits album? Are you sure? Indeed, there have been no less than three dozen “hits” compilations for Kenny Rogers since the release of 1980’s Greatest Hits. Nothing, however, will ever top that 12-times platinum monster, largely due to the fact that it was Greatest Hits where “Lady” first appeared. Written and produced by Lionel Richie, “Lady” was the song that definitively moved Rogers over from country crooner to pop balladeer, and became arguably his most memorable song next to “The Gambler” and “Islands in the Stream”.

The fact that it premiered on his Greatest Hits set was notable; although the practice had been around for years, no artist had ever capitalized on its success quite like Rogers did. Fans loved the song, went out to snag it, but were incentivized to buy its parent album because, ‘lo and behold, all the other Kenny Rogers hits they could ever want were also in this one place. Try as he might, Rogers was never an album artist, and the fact that not a single compilation has even come close to matching the success of his 1980 hits release tells you all you need to know about how effective this method was.

5. George Strait – “I Hate Everything” (50 Number Ones, 2004)

You want audacious? Here’s audacious: putting out a double-disc compilation called 50 Number Ones and having a 51st song on there … that just so happens to also go to number one on the Billboard Country charts. Believe it or not, Strait has churned out “Greatest Hit” number ones before, like “The Best Day” from 2000’s awkwardly-titled Latest Greatest Straitest Hits and the overly sentimental “Check Yes or No” from 1995’s Strait Out of the Box. Yet “I Hate Everything” remains the best of the bunch: a straightforward strummer of a ballad that mixes his trademark sentimentality with a good dash of humor (“And if it weren’t for my two kids / I’d hate my ex-wife”).

Although Strait didn’t write this song, it still was representative of his best qualities, sounding simultaneously very modern and undeniably classic at the same time. The tune could’ve been released in 1978 without much of anyone noticing the difference. He’s had big hits since then, but “I Hate Everything” is one people keep coming back to, as the song inverts clichés by playing into them wholeheartedly, making for one of the hands-down best songs in his already-storied discography.

4. Madonna – “Justify My Love” (The Immaculate Collection, 1990)

Let’s take a second and acknowledge just how goddamn weird “Justify My Love” is as a song. It features a minimalist drum beat, a lot of reverb-heavy vocals, a wheezing old synth line, and… well, not much else. A lot of the song’s popularity can be attributed to its sexually explicit music video, but Madonna knows that controversy sells, and as the lead single to The Immaculate Collection, it helped propel that compilation into the stratosphere, eventually becoming one of the single best-selling albums in all of history. It’s even more astonishing given that this song, co-written by Lenny Kravitz and Prince protégé Ingrid Chavez, remains iconic but only in the most beguiling of ways.

The verses sound like softcore pillowtalk, the chorus being nothing but the title repeated ad nauseum. Somehow, it works. This is a sexy slow jam of a number that wants to be nothing more than the soundtrack to your lovemaking, succeeding at its singular goal by refusing to overcomplicate things, relishing in being the weird little one-off that it is. So iconic was this number that Jay-Z even tried to get Madonna herself to do vocals on the track “Justify My Thug” from 2004’s The Black Album. It was a convention-breaking chart-topper, but for Madonna in the ’90s, that was pretty much her default setting anyways.

3. Tom Petty – “Mary Jane’s Last Dance” (Greatest Hits, 1993)

There are two new songs on Tom Petty’s 1993 compilation Greatest Hits: one is a cover of the Thunderclap Newman tune “Something in the Air”, and the other is “Mary Jane’s Last Dance”, a bluesy little churner that sounded like it fit perfectly in with the likes of “Don’t Come Around Here No More” and “I Won’t Back Down”. Despite the acclaim of Damn the Torpedoes and his more pop-inclined solo effort Full Moon Fever, it’s actually kind of amazing to hear how well Petty’s music works in a single-oriented context, as “American Girl” still makes a hell of an album opener no matter which disc you put it on.

Still, “Mary Jane’s Last Dance” is far from a typical single (something that becomes even more evident when coupled with its faux-horror music video), but it’s still just so fundamentally Petty that it’s hard to deny its place amidst other iconic numbers like “Runnin’ Down a Dream”. Properly credited with the Heartbreakers in full and featuring a nice production assist from Rick Rubin, “Mary Jane’s Last Dance” did what few other Greatest Hits singles could truly do: not only become a Top 20 winner by itself, but also further enhance the legacy of an artist that we already thought we knew so well.

2. Depeche Mode – “Only When I Lose Myself” (The Singles 86>98, 1998)

There has never been a lack of Depeche Mode singles — ever. They released material every single year in the ’80s and dropped a healthy amount of tracks in the ’90s as well, but it was in 1998 when the band dropped a new jam to help promote their new singles comp, and man, was it freaky. Sure, “Barrel of a Gun”, the lead single from 1997’s Ultra, was plenty bizarre, but for those who weren’t fans of Ultra‘s non-stop guitar fuckery, “Only When I Lose Myself” feels like a breath of fresh air, a deeply ’80s-indebted slice of electro-goth weirdness that actually feels like a distillation of the band’s entire aesthetic in one single go.

Sure, “Personal Jesus” and “Enjoy the Silence” may serve as the group’s signature numbers, but if one were challenged with finding a single song that exemplifies Depeche Mode’s entire sonic template, you would be hard-pressed to find a more appropriate number than “Only When I Lose Myself”. The song, a single sandwiched between Ultra and 2001’s Exciter that sounds like it belongs on neither one, is a glorious one-off that conjures the ghosts of past greatness without ever once feeling like it is pandering: an astonishing accomplishment.

1. Janet Jackson – “Runaway” (Design of a Decade 1986/1996, 1995)

We’re just as surprised as you are. Following the unstoppable hit parade that was Control, Rhythm Nation 1814, and janet., it was obvious that not only was Janet Jackson on a roll, but her collaborative relationship with producers Jimmy Jam and Terry Lewis was yielding unprecedented rewards. When working with Jackson, these former Prince band members discovered a sound that hit that pop music sweet spot time and time again. Yet “Runaway” wasn’t just a big, breezy, open-sky pop number: it became what is arguably her all-time signature song.

Sure, fans can make arguments for “Rhythm Nation” or “What Have You Done for Me Lately?”, but hearing those multi-tracked “yeahs” at the end, her sweet come-ons coupled with that vaguely worldbeat instrumentation and that earworm of a chorus — simply put, this is it. This may very well be the single most definitive Janet Jackson song ever, and it was the lead single from her first Greatest Hits compilation. Even more so than Lenny Kravitz’s “Again” or even Kenny Rogers’ “Lady”, having your most recognizable-ever hit come off of a compilation is a pretty astounding accomplishment no matter which way you chalk it up. Her greatest hit came from her Greatest Hits, and it’s for that reason alone that Janet occupies the top spot.

None of you reading this are greenhorns when it comes to “Greatest Hits” compilations. We all know the gamut: by creating a goto catalog release that will entice casual fans for years and decades to come, Greatest Hits/Best Of compilations are a reliable source of income for record labels and artists alike. We all snicker whenever an artist feels the need to tack on a “Volume One” onto that title, because unless you’re the Eagles or Billy Joel, you ain’t gettin’ a Volume Two, rest assured.

Yet instead of simply rounding up popular radio favorites in one place, many labels and artists may want to capitalize on these compilations the best way they know how: by tossing bonus tracks, collector’s-only rarities, or even full-blown singles into the mix. Sometimes, despite the obviously pandering nature of, say, the 2002 Nirvana compilation simply titled Nirvana, the sole new song, “You Know You’re Right”, was downright fantastic. In such a case as that, it was that very add-on that made it worthwhile for even the most hardcore of Cobain enthusiasts. As a marketing ploy, this technique often works, even if the new song in question turns out to be hot garbage — looking right at you, Robbie Williams’ “Radio”.

You’d be surprised at how fertile a market this is, and in culling a list of the 11 greatest “Greatest Hits” songs ever, you discover reams of truly great songs (The Cars’ “Tonight She Comes”, Bruce Springsteen’s “Secret Garden”, Basement Jaxx’s “Oh My Gosh”), fair-to-middling numbers (the Smashing Pumpkins’ “Untitled”, Chayanne’s “Y Tú Te Vas”, Manic Street Preacher’s “There By the Grace of God”, Eminem’s “When I’m Gone”), and cuts that were clearly not included on any of the artist’s “real” albums for very good reason (Billy Joel’s “You’re Only Human (Second Wind)”, The Killer’s “Shot at the Night”). Trust us: we could keep rattling these off until your browser crashes.

So for this list, we looked not so much at the commercial success of these Greatest Hits’ singles so much as the quality of the finished songs themselves, coupled with how iconic this supposedly one-off little number became in the artists’ discography. On top of that, the single in question must have premiered on a Greatest Hits compilation, thus leaving things like “Sweet Dreams ’91” by the Eurythmics out of contention, given that the original song in fact debuted on a much earlier LP. We were genuinely surprised with how the rankings played out (which is why we felt generous by giving 11 spots instead of just 10), but even more than that, we want to hear your own picks in the comments below. This is a strange and fertile subgroup of pop nostalgia here, but it’s high points are downright untouchable.

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This article originally published on 4 February 2015.