“He was standing right next to me looking at CDs. He had this exact [Jesus piece] chain on and I remember seeing it out of the corner of my eye, it was gleaming. I looked up and was like, ‘Oh my God!’” 21-year-old Scott Mescudi blurted to himself as he browsed CDs he couldn’t afford in the old Virgin Megastore in New York’s Times Square.

“I remember me just going like, ‘I’m Scott, man. I’m from Cleveland, Ohio.’ And I remember him being like, ‘Hold on one second. Aye man, I’ma call you right back.’ And him being like, ‘Yeah, so what’s up?’ Like, getting off his phone. And I was like, *jaw drop* ‘I—I’m from Cleveland and I do music. I really wanna be signed. Can you sign me?’”

The year was 2005. The Pats had just beaten the Eagles in the Super Bowl. The Internet domain “YouTube.com” had just been registered. And a 28-year-old Kanye West was the hottest new rapper in the game, a charming, plucky and preternaturally confident underdog who just days before had stolen the show at the 47th Annual GRAMMYs with an impassioned performance and inspiring victory speech. He also happened to be who Scott Mescudi was not-so-convincingly pitching himself to.

“He was like, ‘Man, I got so many artists I’m tryna deal with right now. Unless you on some Biggie and 2Pac-type stuff…’ And I was like, ‘Nah, I’m not that good, but I have the potential for greatness.’ I remember saying that. He was like, ‘What you say your name was again?’ I was like, ‘Scott, but my rap name is Kid Cudi. You definitely gon’ see me again.’”

Like Kanye West a few years prior, Scott Mescudi had recently dropped out of college, left his home in the Midwest and flown East with a couple dollars ($500, cash), a couple dreams (rapper, actor) and a crappy demo (Rap Hard, recorded under his old rap name Kid Mescudi). As his favorite rapper Snoop Dogg once said, New York, New York, big city of dreams. Unlike Roc-A-Fella’s college dropout, however, Scott didn’t have JAY-Z on speed dial. Or any career prospects at all. Even with his head in the clouds, though, Scott knew his first priority in this new city was to find his feet.

While staying with his uncle, the jazz drummer Kalil Madi (“Shout out to the Madis / My bloodline runs deep”) in the South Bronx, Scott spent his first five months in New York trying to find a job—any job—with little success. So desperate was his pursuit of minimum wage stability that he didn’t write or record any music during this time. Even buying music was out of the question, which makes his chance encounter with Kanye West all the more ironic.

Mescudi’s persistence eventually paid off and he landed a job at American Apparel—the kind of retail work that would keep him (and his dreams) afloat during those early years in New York. On the side, he did some modeling and acting. Aware of his musical aspirations, Scott’s agent hooked him up with an audition with two local producers who were looking for a new artist to work with. He won the audition out of “370-something” people and worked with the producers for almost a year, during which time he put together a demo (the name of this one remains a mystery).

With music to shop, Cudi and the producers took meetings with various labels in NYC. In 2006, they visited the offices of hip-hop powerhouse Def Jam, where Cudi met and gave his demo to an A&R named Patrick Reynolds, aka Plain Pat. Whether good fortune or fate, Pat also happened to be Kanye West’s A&R (Pat, alongside Ferris Bueller, hosted Kanye’s 2003 mixtape Behind The Beats, and would later do the same for Ye’s pre-Graduation mixtape Can’t Tell Me Nothing).

The meeting didn’t amount to anything, and soon after, both Cudi and Pat left their respective situations. Eight months later, however, the pair bumped into each other at a party where Pat told Cudi he had kept his demo CD in his car. The two stayed in touch, built a friendship and eventually started working together, with Pat juggling the roles of manager, producer and DJ. Naturally, Pat would play Cudi’s music for his guy Kanye from time to time. Ye liked what he heard.

Around this time, Cudi would meet another person who’d become integral to his career. By '06, he was folding jumpers at Abercrombie & Fitch to fund his rap dreams (and occasionally feed himself). A co-worker, Riliwan (who himself is a rapper under the name Rilgood), introduced Cudi to his friend, Oladipo Omishore. Dot Da Genius, as he called himself, was an electrical engineering student at NYU who had recently started making beats out of his studio at his parents’ house in East New York, Brooklyn. Cudi and Dot became fast friends and close collaborators, developing their chemistry during studio sessions after work and on weekends.

Dot Da Genius and Kid Cudi

While Kid Cudi the artist was slowly finding his sound, Scott Mescudi the person was still struggling to find his feet. Months earlier, his uncle had pressured him to move out —souring his relationship with his nephew—and Cudi was now crashing with a friend in Staten Island, sleeping on a basement floor on which his spine found little comfort for the better part of 10 months. Then, on New Year’s Eve 2006, Cudi was handed an eviction notice. Desperately lacking options, Cudi mentally prepared himself to swallow his pride and temporarily move back to Cleveland.

“I got evicted on New Years Eve, right before I was about to go out. And I remember being like, “Shit — what am I going to do? I’m going to have to go back to Cleveland, go back to my old job, stack some money and then come back.”—Kid Cudi, Complex (2012)

That’s when Dot’s family took him in.

“I went up to his parents’ room, and his dad was like, ‘O-Dot told us about your situation, and we’ve seen that you come to the house, working with Dipo. You guys have been productive, staying out of trouble, and you guys are working towards something.” And he was like, “I think about it like this, if it was my son, what would I want another family to do for my son?” Long story short, he said, “You can stay here as long as you like, until you get on your feet. And you can still work with Dipo. You guys can still work on your music. So it’s a win-win.” “I remember being like, “Holy shit. Like, really?” [Laughs.] Because I was really about to go back home, and I ended up staying there, and the rest is history. It was really, really an amazing thing.”—Kid Cudi, Complex (2012)

With Cudi living down the hall, the budding duo began to tap into a unique musical frequency and hone their formula. The process was organic and collaborative: Cudi would bring hooks and melodies to Dot, Dot would play beats and sounds for Cudi, and together they’d grow these seeds into songs. Dot’s parents nurtured this energy with a strict but supportive environment.

Almost two-and-a-half years after arriving in New York, Cudi had finally found some sense of stability, a stepping stone that seemed to point in the direction of him realizing his dreams. But there was still no sign of a finish line to his pursuit of happiness. Cudi’s older brother, Domingo, was facing “bogus charges” back home, late-night studio sessions put pressure on his precarious day jobs, and with Dot spending most of the week at college, life at the Omishore’s could be pretty gloomy—literally.

“It was a point in time where I would cop bud, listen to Ratatat for hours and hours on end, and just…write songs about myself. The lightbulb in my room didn’t work so the only thing illuminating my room was the sunlight. I had this little window in my room but it was facing a brick wall, so the only thing I could look at out my window was this brick wall. So when the daylight went, it was a wrap. And I would just sit there… and write… and zone out. "It was a very, very, very dark, gloomy shadow over my life at that point in time.”—Kid Cudi, KarmaloopTV (2009)

On one of these dreary nights in early 2007, Cudi was onto something. Inspired by loneliness and job struggles, Ratatat and Geto Boys, a strained relationship with his uncle (who passed away in May that year) and the best strains he could get his hands on in East New York, Cudi wrote a hook and melody that he presented to Dot down the hall. Two days later, the song was finished. They called it “Day 'N' Nite.”

“Day 'N' Nite” was immediately different. Dot Da Genius’ production was minimal, spacey and hypnotically head-banging (no pun intended). Cudi’s lyrics dealt with loneliness, unrequited love and escaping depression through drugs—topics that weren’t largely discussed by rappers, especially not with this level of vulnerability. And he wasn’t simply rapping these lyrics, but singing them with a natural sense of melody and mood. The whole package was intriguing, intoxicating and innovative. The lonely stoner had struck gold.

Soon after he and Dot finished the song, Cudi quietly uploaded “Day 'N' Nite” to his MySpace page, back when MySpace was the place for unsigned artists to be heard and for everyone else to savagely rank their friends. The song wasn’t exactly an overnight success—partly because Cudi only had a couple thousand MySpace friends, and partly because the Internet in 2007 wasn’t regularly catapulting virtually unknown artists into viral stars like it is today. Instead, “Day 'N' Nite” was a hidden gem that slowly found its way to Internet-savvy music nerds who mattered.

Emile Haynie, a producer from Buffalo, New York who had done album cuts for Raekwon, Ghostface Killah and Obie Trice (and has since worked with everyone from Kanye West to Lana Del Rey), was one of those music nerds.

“I found Cudi browsing MySpace one day. He had ‘Day 'N' Nite’ on his MySpace and it had like, a few hundred listens. And I’m like, ‘Who the fuck is this? This song is a smash. This dude is incredible and he doesn’t sound like anything I’ve ever heard,’” Emile told Complex. “And I’m looking at his Top 8 friends, and I see Plain Pat. So I call Pat, and I’m like, ‘There’s this fucking guy, he has this amazing song, and you’re in his friends.’ And he’s like, ‘Yeah, he’s this new guy I got, I think I’m gonna manage him. That’s my dude, we’re just starting out. You should produce some shit for him.’”

Soon after, Plain Pat brought Kid Cudi to Emile’s studio in SoHo and, just like with Dot Da Genius, the two clicked immediately. That same day, they recorded a song called “Bigger Than You,” a soaring soundtrack to solitude, strangeness and space exploration. In other words, a perfect Kid Cudi song. (“Bigger Than You” would’ve been the intro to Cudi’s 2009 debut album Man on the Moon: The End of Day had it not leaked prematurely.) It was a no-brainer: Emile Haynie joined The Kid Cudi Project.

“Day 'N' Nite” continued to quietly simmer on MySpace, but Cudi didn’t just sit back and wait for the song to reach the right people; sometimes he had to go and get it himself. That June, Cudi managed to get into the party for Kanye West’s “Stronger” video premiere in NYC. While there, he asked A-Trak, Kanye’s DJ at the time (and, coincidentally, the guy responsible for putting Kanye onto Daft Punk), if he could play “Day 'N' Nite.” A-Trak kindly obliged.

“In those days, Cudi had a very earnest demeanor. His enthusiasm was almost child-like. He was full of wonder,” A-Trak says. “I remember DJing Kanye’s ‘Stronger’ video premiere, and Cudi was just watching me DJ, in amazement. Honestly, I wasn’t doing anything fancy that day [Laughs]. And yes, he asked if I could play his song at one point. Seeing his song being played by an actual DJ just blew his mind. It’s as if it meant that the song was real.”

According to Cudi, Kanye liked the song and gave him a nod of approval from across the room. “He was like, ‘Yo, you have a lot of shit I’ve heard that I fuck with,’” he told Complex.

Cudi and Kanye would cross path twice more around this time. Once, at the BAPE store in SoHo, where he worked between ’07 and ’08 and would get through shifts by playing Graduation (“Ye came in there one day and I had to chase him out ’cause he had left the sensor on his bag and it was beeping and shit. Imagine, the last thing you want to do is run after a motherfucker like him. But that was funny having to be like, ‘Oh man, you left your sensor on your bag. I was the kid that forgot to take it off,’” he remembered).

And later, in the streets of New York with producer 88-Keys, who formally introduced them. “I kept telling Ye how ill Cudi was on coming up with crazy melodies to beats & how his lyrics really put you in outer space. Man On The Moon/Loner type shit for real!” 88-Keys wrote on his blog. “Weeks later, I’m back @ Kanye’s crib one late morning, paying him a visit. We hang for a few then I bounce because Kanye’s about to have a business meeting… So about 6 city blocks away from his crib, who do I run into? Mr. SoLo DoLo himself. I tell him, ‘Yo I just talked you up to Kanye. I just left his crib a few minutes ago.’ Cudi got a little hyped like, ‘Word? What’d he say? Did you play him our joint? What’d he think?’ Now as I’m telling Cudi Kanye’s comments who do I see walking down the street? The Louis Vuitton Don himself. So I gave them the formal introduction.”

Kanye wasn't ready to sign Kid Cudi just yet, no matter how many times he bumped into him. Instead, it was A-Trak, who had been obsessively bumping “Day 'N' Nite” after Plain Pat had sent him the song, who took a chance on the kid from Cleveland. In November 2007, he signed Cudi to a 12-inch deal with Fool’s Gold, the indie label he founded with fellow DJ Nick Catchdubs earlier that year.

“The sound of hip-hop was really changing at that time. I’m not even sure if I understood what was great about the song yet, I just knew it was hypnotic, and Pat and I decided to try it out on Fool’s Gold,” A-Trak remembers. “It might seem surprising that he brought it to me since he had a job at Def Jam, but he must have known that the majors were not understanding this shift yet.”

With the pieces in place—Pat and Emile managing and producing him, A-Trak signing him, Dot living and working with him, Kanye aware of his existence—Cudi hunkered down at Emile’s studio in SoHo and got to work on his debut mixtape, A Kid Named Cudi.

Where the previous year was welcomed with an eviction notice, 2008 got off to an auspicious start for Kid Cudi. In February, Fool’s Gold officially released “Day 'N' Nite” as a single, accompanied by an electronic remix by fellow Fool’s Gold signees Jokers of the Scene and a B-side cut called “Dat New New,” another Dot Da Genius collaboration that Cudi had previously uploaded to MySpace.

With Fool’s Gold’s eclectic, International audience to tap into, “Day 'N' Nite” quickly caught the ears of Italian electronic duo Crookers, who fell in love with the song and asked to remix it for kicks. The following month, Fool’s Gold released the remix as a free download, and it proved to be the most crucial boon to “Day 'N' Nite”’s success.

Crookers’ remix—which transformed the lonely stoner anthem into a club banger—slowly grew Cudi’s popularity outside of both hip-hop and the United States. Soon enough, he was being booked for International shows, including a two-week tour of Australia between late June and early July, which meant Cudi quitting his job at the BAPE store—a stable, sought-after gig he landed on his fourth attempt. “All the good things in my life happened because I took chances,” he said.

After arriving home from Australia, where he performed at packed houses in some cities and near-empty ones in others, Cudi had no job and no guarantee that music would pay off. This uncertainty festered for just three days before he got a call from Plain Pat.

“[Pat] was like, ‘Yo…so Kanye wants you to come to Hawaii.’ I had already met [Kanye] in passing but this was like the actual up-close-and-personal [meeting]. He’s like, ‘Yo! What’s up? Welcome, man! Aye, you ready?’ I’m like, ‘Yeah!’ ‘Alright, I got some beats I’ma give you on the jump drive.’ “I was smoking Newports at the time so I go out on the patio. I’m sitting out there, I’m so fucking nervous [Laughs]. I got my laptop set up. He comes out with the jump drive, he’s like, ‘Just have fun.’ I’m like, ‘Alright.’ I start vibing. It’s like eight of the most wonderful beats. I think seven of them were used on that album. “First beat I listened to, I’m like, ‘Alright, this shit is dope as fuck, of course. It’s Kanye West! What the fuck am I gonna do?’ [Laughs]. And they’re like, ‘Hey man, we’re working on The Blueprint 3. We want you to write hooks. That is the song essentially. Go!’ “I think I was vibing for about 5, 10 minutes, he comes back and he’s like, ‘So what you got?!’ [Laughs] I’m like, ‘Oh shit! Oh man, I got like one idea. I don’t know if it’s any good.’ He’s like, ‘Just tell me, what is it?’ I’m like, ‘Okay… *clears throat* Ohhh, they want me to fall / Fall from the top / They want me to drop / They want me to stop / They want me to go’ — ‘Alright, alright, alright! Go in the booth and lay it down right now!’ ‘Are you sure? Do you like this?’ ‘Yeah, come on, come on!’ *Boom* “‘Alright, you got another one?’ ‘Oh man, I had one I was starting but I don’t know if it’s any good.’ ‘Just go in there and lay it’! ‘Okay… Cooking’ up in the kitchen / Young boy had that vision / Had to get with it / Oooh, oooh, oooo-ooooh.’ Cause we was like, ‘Oh it’s for Jay. Let’s make a theme for dope boys in the kitchen.’ This was going crazy, you can see people through the glass like, ‘Aaaaah!’”—Kid Cudi, OTHERtone (2016)

After returning to New York (again) with an official Kanye co-sign and fire in his belly, it was time for Cudi to take center stage. On July 17, he released his debut mixtape A Kid Named Cudi, presented by Fool’s Gold and streetwear brand 10.Deep.

A mix of original songs (produced by Plain Pat, Emile Haynie and Dot Da Genius among others) and eclectic remixes that reflected his left-field sensibilities (OutKast, Ratatat, Paul Simon), A Kid Named Cudi found Kid Cudi carving out his own lane entirely, right at the forefront of the hip-hop's future. “Cudi Get” and fan favorite “Maui Wowie” showcased his fun, carefree side; “Embrace the Martian” and “Cleveland Is the Reason” laid the blueprint for Cudi’s distinct Man on the Moon sound; “Man on the Moon (The Anthem)” and “The Prayer” doubled up as painfully vulnerable confessions—the kind of sad, lonely and intimate anthems that have defined Cudi’s career.

A Kid Named Cudi dispelled any notion of Cudi being a one-trick pony; in fact, the only 24-year-old with more ups in the Summer of ’08 was Andre Igoudala. Except this rookie had an entirely different vision of the game than everyone else. “I would play all my stuff for everybody and all the people would give me feedback and they’d be like, ‘Yo, why yo shit sound so different?’ Like that’s a bad thing,” Cudi says on “Man on the Moon (The Anthem).” “And I be like, ‘Why not?…Nigga.”

To get the full story behind the making of A Kid Named Cudi requires a roughly three-hour sit-down with the Rosenthal brothers, not to mention SEAL Team Six’s finest to get Kid Cudi, Plain Pat and Emile Haynie—who are as elusive as they are talented—in the same room. But what Emile (who was only slightly easier to track down than Cudi and Pat) does remember is the magical energy of those sessions in his studio on Broadway and Spring.

“I remember meeting Cudi and within seconds realizing he was special. Someone magical and a personality I hadn’t come across yet. It was the first time I felt like I was working on something truly new and important. I had worked with some great artists before, but Pat and Cudi were something new and totally different from anyone else,” he says.

“Even though it was a mixtape and a lot of the beats we used were revamps of existing songs, Cudi’s take on everything was so fresh that it felt like an album. I knew he was going to change things and I was so happy to be along for it. We went on to make two more full albums together but A Kid Named Cudi is the one I look back on with the most fondness.”

L to R: Emile Haynie, Kid Cudi and Plain Pat

The night of A Kid Named Cudi’s release, Fool’s Gold and 10.Deep hosted a party at the Red Bull Space in NYC. Nick Catchdubs, Plain Pat and 88-Keys played DJ sets while Cudi coronated his mixtape with a headlining performance. Emeka Obi, former 10.Deep marketing manager who proposed the A Kid Named Cudi collaboration, recalls the buzz around the party.

“By the time the party had come to fruition, ‘Day 'N' Nite’ had really started making the rounds. So the energy was there, the excitement was there,” he says. “I get to the space and there was already a line at like 5, 6 p.m. There was a long ass line going around the corner. From then on, the line got longer and longer and the anticipation got more and more fervent.”

Right before Cudi was about to go on stage, that’s when Kanye showed up.

“Pat hits me up like, ‘Yo, I’m bringing Kanye. Meet me outside.’ So we sneak Kanye in through the side entrance—and this is height-of-popularity Kanye, he was really getting to be Big Kanye. So to have him there was a big deal,” Obi says. “The creativity and the charisma and the swag and all the other stuff that was coming off of Cudi that night was palpable in the room. You could see that [Kanye] saw what we saw in him that night.”

A-Trak: “I do remember spotting Paul Rosenberg at the event. Paul was Eminem’s manager. That surprised me. It was indicative that people were starting to notice Cudi in the industry.”

By this point, it was obvious that Kanye saw in Cudi a creative protégé, if not a collaborative partner. In September 2008—three-and-a-half years after begging Kanye for a record deal in the Virgin Megastore—Cudi signed to G.O.O.D. Music.

The stuff Plain Pat played him intrigued him, the mixtape impressed him, but according to Cudi, it was “Day 'N' Nite” (which, thanks to an unlikely Jim Jones remix, was becoming popular with mixshow DJs) that convinced Kanye to do the deal. “Everywhere Kanye went out, like to the clubs, he said that he heard my song and motherfuckers would go crazy,” he said. “There was a time where he said he was in club with Jay in Paris or somewhere, and it came on, and motherfuckers’ reactions was just crazy.”

Perks of joining the Grammy Family—aside from the immediate popularity boost, of course—included opening for Kanye on the UK leg of his Glow In the Dark Tour and making more trips to Hawaii, where he helped craft Ye's fourth album 808s & Heartbreak.

Recorded in three weeks during the fall of 2008, 808s was, of course, inspired by the loss of Kanye’s dear mother, Donda West, as well as the break-up with his then-fiancée Alexis Phifer. Sonically, there’s a case to be made that Cudi’s melodic, confessional crooning on A Kid Named Cudi—lyrics from which Kanye would quote back to Cudi—influenced the album’s sparse and vulnerable sound. In any case, he contributed vocals to two songs (“Welcome to Heartbreak” and “Paranoid”) and co-wrote two more (“Heartless” and “RoboCop”).

Kid Cudi and Kanye West’s creative kinship was officially born; at that moment, you could hear the creaking of hip-hop changing its course. “Me and Cudi are the originators of the style, kinda like what Alexander McQueen is to fashion, everything else is just Zara and H&M,” Kanye once bragged.

By 2009, Kid Cudi was unfuckwittable. “Day 'N' Nite” climbed to No. 3 on the Billboard Hot 100, just as the Crookers remix became a top 20 hit across Europe (“the fact that we had two entirely different versions of the song climbing their respective charts at the same time was unbelievable,” A-Trak says); he signed to Universal Motown after fielding offers from every major label imaginable; and released his debut LP Man on the Moon: The End of Day, an album that solidified Cudi’s star power and left its own indelible mark on hip-hop.

Outside of the studio, Cudi appeared on XXL’s 2009 Freshman cover, back when the Freshman cover meant something; headlined the Great Hangover Tour with Asher Roth; collaborated on a “Baby Milo” T-shirt with BAPE, just over a year after quitting his job there; and realized his acting dreams by landing a lead role in the HBO series How to Make It In America. Scott Mescudi was no longer just a kid named Cudi; he was Kid Cudi.

Of course, fame and success have also come at a costly price for Kid Cudi. The years since A Kid Named Cudi have been marred by drug problems and legal troubles, scuffles with fans and beef with other rappers (including, briefly, Kanye), creative misfires and retirement threats. Not to mention continued mental health struggles for which he checked himself into rehab at the end of 2016 (thankfully, it appears he’s reborn).

Perhaps at the time, it was slightly overshadowed by everything else that was happening around it: “Day 'N' Nite,” 808s & Heartbreak, Man on the Moon. But looking back 10 years later, as the mixtape has matured into a cult classic like much of Cudi’s non-Man on the Moon work, it’s difficult to understate the importance of A Kid Named Cudi. Zoom out and you’ll see a career taking shape, friendships being formed, a genre being changed. Zoom in and you’ll see a snapshot of those precious moments right before Scott Mescudi’s dreams came true.

“In a way, when I think of A Kid Named Cudi, that mixtape happened right before he really blew up on a whole other level,” A-Trak remembers. “So many people look at Cudi as an artist who deeply impacted their lives, who made them feel less alone, and who created an entirely original sound. This mixtape was before any of that effect was felt. It was just Cudi and his friends making songs and hoping that people would like it.”