Few artists, upon their death, have left as big a hole in their wake as Princedid. When Prince ed away in 2016, for a brief moment, it was as if the world had stopped turning. Along with his band, the Revolution, Prince was a multi-talented, genre-bending music master and aficionado, whose vocal and musical prowess knew no bounds. With a collection of Prince has released over three dozen studio albums, including one posthumous album, and has sold over 100 million records worldwide throughout his career.

One of the most prolific careers in music history, full of iconic music videos and some truly legendary live performances, it's difficult to characterize Prince as an artist with just a handful of albums, let alone a handful of songs. As we come up on the ninth anniversary of his death, it's the time of year that Prince fans everywhere play his music in remembrance on repeat. I thought it pertinent to take a look back at ten of the greatest hits that truly defined that incredible career, and the kind of musical talent that really only comes around once in a lifetime.

1 1999

The Party song of the '80s

While on tour, Prince saw a documentary about a Nostradamus prediction of a mass apocalyptic event that would wipe out all of humanity in the year 1999 (via The Current). Given the fear of that catastrophe, Prince envisioned a future where the entire population would spend the whole year leading up to the new millennium constantly partying. Thus, the song "1999" was born, encoming both that feeling of pure chaos, and wanting to savor the relative calm before the storm.

Prince wrote about anarchy and destruction resulting from both Nostradamus' prediction and the violence across humanity at the hands of one another that was already taking place at the height of the Cold War. This is a song whose lyrics, when you really listen to them, are much darker than you would expect given the upbeat nature of the song, and the chorus, which explains: "Tonight we're gonna party like it's 1999." And that was a lot of what Prince was all about: exploration of duality. The yin and yang effect; where there is light, there must be dark, and vice versa.

2 Let's Go Crazy

For the Simple Love of Life

One of the most iconic intros of Prince's career comes in the form of a preacher's sermon at the beginning of "Let's Go Crazy." The song starts out with a sequence reminiscent of a wedding, with an organ accompanying him:

Dearly beloved

We are gathered here today

To get through this thing called "life"

Electric word, life

It means forever and that's a mighty long time

But I'm here to tell you there's something else

The afterworld

The contrast between life and death is poignant in this track, yet another upbeat, feel-good, make-you-want-to-dance tune. The chorus, "Are we gonna let the elevator bring us down? / Oh no, let's go," is just as iconic as the introduction to "Let's Go Crazy," and it's nearly impossible to hear these lines and the beat that follows, and not tap your feet at the very least.

Another iconic element of "Let's Go Crazy" is the ear-shredding guitar solo that comes at the very end of the song. He starts to tease the guitar a bit as the lyrics drop off, Prince singing, "He's coming," over and over, referring to the Grim Reaper. He then launches into a solo that proves he's not only a lyrical and vocal master, but a master of guitar, too. The solo, and subsequently the song, comes to a close with Prince shouting the line, "Take me away!" leaving the listener on a truly extreme musical high.

3 Kiss

Iconic In Its Own Right, Even More So Because of Julia Roberts

Prince's vast vocal range is hardly a secret, but perhaps the clearest showcase of just how broad that range is comes from his perfectly pitched falsetto in "Kiss." He makes reaching some of the highest notes of any singer, male or female, seem genuinely effortless. The song kicks off with a simple guitar strumming, done in a way that only someone as prolific as Prince could make famous, followed by a low grunt that makes the lyrics to follow sound almost jarring in contrast. As if Prince alone didn't get everyone to sing these lyrics along with him, Julia Roberts sure did.

You don't have to be rich to be my girl

You don't have to be cool to rule my world

Ain't no particular sign I'm more compatible with

I just want your extra time and your kiss

In one of the most famous scenes from the movie, Pretty Woman (1990), Roberts' character is sitting in a hot tub with her headphones on, jamming out to the song, singing the lyrics out loud. While "Kiss" was definitely a successful Prince song already, it was propelled even further into the cultural spotlight by this scene. One of the most famous actresses of the century, singing it in one of the most famous scenes of one of the most famous movies of the century, certainly solidified the song's place in 20th-century pop culture.

4 Raspberry Beret

A String and Keyboard Masterpiece

Off the 1984 album, Around the World in a Day, "Raspberry Beret" is a song that features a remarkable number of different string instruments, including 12-string acoustic guitar, bass, cello, and violin. The song begins with a percussion ensemble, before the classical string instruments take hold of the track, launching into a beautifully composed introduction. The pseudo-orchestra continues to play as Prince's vocals start in, detailing a nostalgic '80s love (or lust) story.

"Raspberry Beret" is so masterfully composed that, at times, it can actually be hard to discern which instruments are at play at a given point during the song.

After the massive success of the albums 1999 and Purple Rain in 1982 and 1984, respectively, "Raspberry Beret" peaked at number two on the Billboard Hot 100, and made another appearance on the chart at number 33 the week of his death in 2016. The track is also dominated by the keys, on top of an electric grand piano, playing the same chord progression as the string instruments and blending together seamlessly. "Raspberry Beret" is so masterfully composed that, at times, it can actually be hard to discern which instruments are at play at a given point during the song.

5 Little Red Corvette

Prince's First Massive Hit

The first single to be released from the album 1999, "Little Red Corvette" was the first instance of Prince cracking the Billboard Hot 100's top 10, with the song peaking at number six on the chart. Like much of his work, this song is loaded with sexual imagery, the car as a metaphor for a woman. Prince wastes no time in the first verse getting the message across that while this may seem like a song about a car, it is actually a song about sex:

See, you're the kinda person that believes in makin' out once

Love 'em and leave 'em fast

I guess I must be dumb 'cause you had a pocket full of horses

Trojan and some of them used

The instrumental ensemble of this track isn't traditional—not that any of his music is traditional, but "Little Red Corvette" is driven primarily by synthesizers and percussion. There is some guitar and some bass, but it’s evident that the synth and drums are the stars of this track. It’s this combination that gives the track a sort of ethereal sound that makes you feel like you’re floating, similar to the feeling evoked by a futuristic ‘80s movie. Coupled with the car metaphors, it's no wonder this song was his first to crack the top 10 of the Hot 100 chart.

6 Purple Rain

The Ballad of Ballads

Quite possibly the most important song on this list, "Purple Rain" remains Prince's most-streamed track. If I absolutely had to narrow this list down to the one singular song that defines Prince's career and I had no wiggle room for a second, "Purple Rain" would be the one.

Among the greatest ballads of all time, this song is quite possibly the strongest Prince ballad, too. It evokes the exact feeling one would expect if they were actually caught outside in a 'purple rain.' This song has a smooth sound, each element from Prince's vocals to the synthesizers and sound effects, the guitar to the drums—they all fit together like the pieces of a jigsaw puzzle.

Quite possibly the most important song on this list, "Purple Rain" remains Prince's most-streamed track.

The lyrics paint a vivid picture, without really even using any imagery beyond the words "Purple Rain." This song was the title track Purple Rain, an album that doubled as a soundtrack for a film of the same name in which Prince starred. Though there are many songs that display Prince's sheer genius, his career and his artistic identity simply would not have been the same without the impact of this song.

7 Sign 'O' The Times

A Show of Synth and Lyrical Prowess

Musically speaking, "Sign O' The Times" is, to put it simply, a weird song. With the occasional—albeit pretty famous—electric guitar riff, this track is driven primarily by a digital synthesizer and an electric drum pad. The title track off of Prince's 1987 album, this song is prolific in that it is likely one of his most experimental hits. The sound of the synthesizer pairs perfectly with the digitally manufactured drum beats, creating a musical backing that, aside from the brief guitar riff, is almost entirely devoid of any traditional musical instruments.

Complementing the synthesizer-led musical backing are some of the most poignant lyrics of any Prince song in his entire discography. In the first verse, he sings:

In , a skinny man died of a big disease with a little name

By chance his girlfriend came across a needle and soon she did the same

At home there are seventeen-year-old boys and their idea of fun

Is being in a gang called 'The Disciples'

High on crack and totin' a machine gun

Prince touches on real issues that were plaguing humanity and were considered taboo in many areas of discourse, and the cherry on top is he called the song "Sign O' The Times." Not to mention the fact that the 'O' in "Sign O' The Times" was meant to be a peace sign. Given that so much of his career was based upon pushing the envelope, no list surrounding Prince's most definitive songs would be complete without this one.

8 I Wanna Be Your Lover

The Hit of His Early Days

The lead single from his 1979 self-titled album, "I Wanna Be Your Lover" boasts a radically different sound than the majority of Prince's later hits. While his talents as a vocalist and musician at large are still on full blast, this track is the best of Prince's early days, before Prince took to incorporating his sexuality and other personal identities into his music on all fronts. At the risk of sounding reductive of this song's merits (of which there are plenty), "I Wanna Be Your Lover" has a more traditional sound than most of his hits.

"I Wanna Be Your Lover" boasts a radically different sound than the majority of Prince's later hits.

Though it didn't quite get him to the status of worldwide phenomenon that we've come to know over the decades, this song was the first Prince song to ever really be considered a hit. After his debut album, For You (1978) had just one song reach the Billboard Hot 100 ("Soft and Wet" which peaked at 92), "I Wanna Be Your Lover" was the song from his second album that started to get him noticed, peaking at number 11. Though it is immediately recognizable as an early song, it still embodies many of Prince’s signature musical elements.

9 When Doves Cry

The First Track to Reach #1

When it was released as a single in 1984, "When Doves Cry" was Prince's first hit single to reach number one on the Billboard Hot 100. Not that fans were unfamiliar with Prince's guitar capabilities, but the way this song opens with a truly face-melting shred of a solo took it to a whole other level. It's almost hard to believe just how crazy he goes in that solo, given that it comes at the very beginning of the song, and only lasts for about 15 seconds before some sound effects, percussion, and eventually keys kick in.

Additionally, "When Doves Cry" is a song in which Prince shows off the other end of his vocal range. Where "Kiss" was a shining example of his high notes, this song exemplifies just how great he can sound when he goes low, too. His vocals throughout this song are deep, almost seductive at times, as he coos along with the famous drum backing. Not only did this song peak at the number one spot on the Billboard Hot 100, it remained there for five weeks; if someone were to assert that this is Prince's single greatest hit, I wouldn't argue.

10 Controversy

A Hint Towards What Was to Come

The title track of his 1981 album, "Controversy" feels like a more developed song from later on in Prince's career rather than the lead single from his fourth studio album. A song that truly lives up to its name, the lyrics of "Controversy" address all the controversy and speculation surrounding Prince's identity, particularly with regard to his sexuality and religion. About halfway through the song, he goes into a monotone recitation of The Lord's Prayer, sandwiched on either side between him repeatedly singing the word "controversy."

On top of the deeply introspective lyricism, Prince takes this opportunity to show off his many musical talents with this song as well. He is credited not only with the lead vocals on the track, but the synthesizers, keys, guitar, and drums, too. Where "I Wanna Be Your Lover," released just two years prior, is more representative of Prince’s early sound, "Controversy" could have been released a full decade later than it actually was, and no one would question it; this song sounds like it is truly ahead of its time in the arc of Prince's artistic evolution.