Asking an artist to choose their best song can be like asking a mother to name her favorite or most successful child—it's never going to be an easy decision, and it's one that most would rather leave to the listeners to consider. But even when it comes to listeners, that discussion can be one of the most fractured conversations in music, with each person enjoying a different aspect of an artist's music.

But XXL wasn't going to let these rappers off the hook with overly-diplomatic answers; we wanted to get right to the source of the creation of some of the best songs of an artist's career, and ask them what they considered to be their best creation. With hundreds, sometimes thousands, to choose from, it's never going to be an easy decision, and as an artist continually pushing themselves forward, looking back on an extensive catalog and picking the one singular high point can be more detrimental than looking ahead to future high points yet to be created.

"We always look at it as, we go through a school of music in your heart, in your mind, and for me I felt like I was getting better as I was going on," Raekwon says when asked to identify his best song. "And now I feel like I'm at a college level of understanding my craft, understanding my rhymes and where I want to go with it. The words are more vivid. I feel like with each album I was supposed to get more better and more craftier. That's what makes us witty, is that we can rhyme about this today and be on a whole different thing tomorrow. So we only get better as we learn more, I guess. That's where I'm at."

With that in mind, XXL rounded up six rappers who, while still saying the best is yet to come, were able to identify a creative high point that stuck with fans and made the song the best of their career so far. Soak it in. —XXL Staff

Prodigy
"Quiet Storm"
Murda Muzik, Mobb Deep
1999
Best Line: "My new edition's way bitchin' / Those that listen / Get addicted to my diction / Fuck rhymes I write prescriptions / For your diseased / Generic rap's just not potent like P's"
Prodigy: The first thing that popped in my head was maybe "Quiet Storm" or "Keep It Thoro." But I don't want to put myself in a box like that was the highlight of my life, 'cause it wasn't. There's still things going on right now that I consider up there with that, even though it's not getting as much marketing, budget and as much publicity as back then, it's still on that same level of quality.

There's certain shit on that Albert Einstein album that I just put out that is incredible to me, that I can still put out, that blessing from God to have that type of creativity still. Something from that album, I would say a song like "Confessions," that's an ill story I'm telling about just having drama in the streets with niggas. That's an ill song. But yeah the first thing that popped in my mind when you asked me that question was probably "Quiet Storm." That's one where I feel that I had reached a level of songwriting that I was looking for. A lot of people like to say, "Yeah, that was when you were at your peak. It'll never be like that again." But that ain't true, that's just somebody's opinion.

Killer Mike
"God In The Building" and "Ric Flair"
I Pledge Allegiance To The Grind Volume II and Pl3dge
2008, 2011
Best Line: "Young player from the South, tell stories like Biggie / Take the King's English, paint pictures so vivid / That the listener will swear to God they lived it / If that ain't God in motion, nigga tell me what is it?" —"God In The Building"
Killer Mike: I don't know, 'cause I've done a lot of good ones. But I'd have to say it would be a tie between "God In The Building I" and "Rick Flair." To me, I love the records riding around in my head, boppin' to it, I think I'm gettin' my rap shit off. But you have to see me perform those two songs live. Like, "God In The Building" brings people to tears when I perform it, 'cause I do it with the beat and then a capella. I end my shows with it, and it literally brings people to tears.

And you haven't seen, to me, a more exciting record than "Ric Flair" performed live. It is just epic. At the end, the beat drops, and people that have never heard the record are singing it. So those are two of the most powerful songs I perform, and they happen to be my two favorite records. The only other one I could have named—which you guys have probably never heard of, it's from a mixtape—is a record called "Niggas Down South," and that one, whew.

Kirko Bangz
"Drank In My Cup"
Progression 2: A Young Texas Playa
2011
Best Line: "I don't ride the toll / Don't pay the change / I'm EZ tag / Like Peter Pan"
Kirko Bangz: Of course the biggest song of my career so far is “Drank In My Cup.” It went No. 1 on the charts for nine weeks. It was the first song that really put me on. That damn song changed my life.

Rapsody
"Lonely Thoughts" (Remix) featuring Chance The Rapper and Big K.R.I.T.
She Got Game
2013
Best Line: "Philly to NY / Just to wet you up I’m tear ducts to a dry eye / My my what he told me / Reciting Obi Kenobi / “You'll be the death of me solely” / I told him showly / I agree I'm Ali / Cross 'em like Doji"
Rapsody: I would probably say "Lonely Thoughts." That's the one that seems to have the most legs to it. Everybody loves the beat, the lyrics, the feature [with Chance The Rapper]. [Laughs] The remix feature [with Big K.R.I.T.]. So I would probably say that one. I think it was more the reaction and how everybody gravitated toward it. The best one I think I've written? Wow, I don't know, man, I have so many. "Lonely Thoughts" is the one. I think, in that space I was in, I wasn't trying to prove anything, I was just doing it for the love of it, for the skill of it. Anything that came to mind, I just wrote it. It just worked out.

Big K.R.I.T.
"Country Shit" (Remix) featuring Ludacris and Bun B
R4: The Prequel
2011
Best Line: "Pull up, hop out, clean / In my old-school time machine / Keep a parachute for this altitude / 'Cause when you riding this high / Make it hard to breathe"
Big K.R.I.T.: The best song of my career, good Lord. Man, I would say “Country Shit,” just because I would say that it was the first song that was more like an introduction to—I wouldn’t say mainstream music—but like the first introduction to radio. 106 & Park. A lot of things came along with that record. That record definitely opened a lot of doors for me as well, festivals and things of that nature, just because of one song. And that was the first time I actually had the chance to work with Ludacris and Bun B. So I’ll say “Country Shit.”

MC Lyte
"Cha Cha Cha"
Eyes On This
1989

Best Line: "My competition, you'll find them in the hospital / Visiting time, I think it's on a Sunday / But notice they only get one day to shine / The rest of the week is mine / And I'll blind you with the science that the others have yet to find"
MC Lyte: You know what, it depends of who you ask. If you ask the record label they would say “Cold Rock A Party" because that sold the most. But “Cha Cha Cha” started number one. I don’t know—the best is so speculative. If I go do a show all along the Eastern shore and I do “Paper Thin,” that’s the best to them. If I do Chicago, it's “Lyte As A Rock.” “Cha Cha Cha” on the West Coast, that’s the best to them.

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