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Drake may be dropping songs called "Trophies" and "We Made It" in recent months, but things weren't always that way; everyone's come up is littered with false steps and awkward movements at some point until something catches. What that moment is is different for everyone. With that in mind, we asked seven rappers—from the old school and the new—to pinpoint the moment they knew they could build their career in hip-hop. We made it. —XXL Staff (@XXL)


Big Boi

"After we hooked up with Organized Noize, and our lyrics combined with their beats just sounded like something special. Once we put out our first song, "Player's Ball," that was a Christmas song on a Christmas album. It went to No. 1, it was like six weeks at No. 1 on the Billboard charts, the single went Gold and everything, and it lived past Christmas, just pretty much telling everyone what we did every day."


Ice Cube

"I guess the minute we put together the N.W.A single, with 'Dope Man' and '8 Ball' on it. I knew this could be a career because people was just loving us and loving our style. I knew if we keep putting out records like this, we just as big as any other rap group out there."


Killer Mike

When everybody who had slept on Pledge 2, and Pledge 3 came back around—and I'll never forget Rolling Stone putting "Ric Flair" in their top 50 songs of the year [in 2011]. And even though I didn't get my picture in it, I remember looking at the other groups—R.E.M. was on the page. [Laughs] And I'm a fan! Of course. I'm like, "I am in Rolling Stone, I'm on the same page as people I grew up idolizing, and people are asking, 'When is Pledge 4'?" That obviously told me, there is a next thing. And the next thing became R.A.P. Music, and the next thing became Run The Jewels, and then Run The Jewels 2, and in 2015, I'm looking forward to some better, crazier shit.

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Big K.R.I.T.

"When I dropped the project See Me On Top I. And it had this song on it called “They Gon' Hate.” And it ended up making it on a mix-tape called Atlanta, and I had never even been to Atlanta at the point in my career. This was like 2003-2002. And I dropped the song and DJ Folk out of Atlanta put it on a mixtape that had Trick Daddy and Jeezy on the front, it was called From The Trap To The Stroll. And that was the first time I had made it into a mixtape, so that was a super duper milestone. So I would say See Me On Top I, “They Gon' Hate” was the first time I made it onto a mixtape."


Kid Ink

"It's not really a moment of making it, it's more a moment of No Turning Back. There were certain moments where I knew this was a moment where I had to take it and go yo, this is it, this is the job I'm supposed to do. There is no real peak or anything, hopefully, to contend with, so I can just work hard always and always, man. I never try to think or live on too many moments, I always try to beat those moments. Keep doing better and better without even thinking about it, and just working hard. And I think that's just how my grind goes, and how I keep it together. But I think there was a moment where I had to make a decision of if I wanted to work at the regular job I had or skip the job that day and go to the studio and probably get fired. And that's what wound up happening."


Kirko Bangz

"Now. I look at it now. These past two months, I know I can make it. I'm making it right now, every single day when I get up I'm doing something every day to better myself in this game. Now is the best time. Now is the moment. Now is what I'm gonna talk about ten years ago, like, this is when I realized what I can be in life. Not even about music, but as a man. This is when I realized that this shit is for real. You only get one opportunity in this, and I keep getting blessed. But I gotta take care of my business, 'cause I won't be around forever. I gotta lay that foundation for me and my family."


Isaiah Rashad

When I was 14 listening to DJ Unk's "Walk It Out" and I wrote a verse after I heard Andre 3000 remix it, that's when I knew I could be a rapper. Actually, after I did this track called "Khaki." After I did that, I knew I could be a rapper. It was just the first couple lines, the first couple lines were pretty clever to me. I used the same lines on "Ronnie Drake." That's how I knew—"So don't call me a nigga / Unless you call me 'my nigga'." That's how I knew.