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.
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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.
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.
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.
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.
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.
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 moreso 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.