The fourth quarter represents the last chance artists have to leave a musical mark on a year. The final deadline to be considered for Grammy nominations falls within this period. It’s also when pundits begin cranking out the requisite end of the year "best of" lists. More than anything, it serves as a moment of metamorphosis, as the new year—and the future—lie on the horizon. Looking back, the fourth quarter of 2009 stands out, not just because it was the close of a decade, but because it served as a pivotal moment of transition in hip-hop.

The catalyst arrived on Sept. 8, 2009, when Jay Z released The Blueprint 3. After dealing Auto-Tune a deadly blow earlier that summer with "D.O.A. (Death of Auto-Tune)," Jay Z released an album that featured a mixture of solidified stars (Kanye West, Rihanna, Young Jeezy, Pharrell Williams, and Alicia Keys) and rising young talent (Kid Cudi, Drake, and Roc Nation’s own J.Cole).

Cole, who became the first signee to Jay Z’s Roc Nation imprint earlier in the year, was just three months removed from the release of his sophomore mixtape, The Warm Up. The North Carolina native—who took an uncommon route to hip-hop success by using college as his vehicle to its mecca, New York City—was given a huge assist on the aptly titled "A Star Is Born." After running through a quick oral history of hip-hop, Hov let Cole loose on the final verse. Five years later, he has two gold albums and has been nominated for two Grammy awards. A star was born, indeed.

In a post-808's & Heartbreak era, a growing contingent of fans were tiring of the superthug persona and searching for music that precisely channeled their perspectives.

A year earlier, Kid Cudi was quietly making a name for himself. Between September and October of 2008, the kid from Cleveland was holed up in Hawaii helping to craft Kanye’s 808s and Heartbreak, an album that would leave an indelible mark on a new set of rappers who were more comfortable experimenting with tone, texture, and form. Cudi lent his talents to The Blueprint 3 in an auxiliary capacity, crafting reference tracks, and contributing the hook to "Already Home." On the song, Jay Z addresses allegations that his presence in rap was preventing other artists from thriving. "These niggas want me to go, don’t they know that I’m gone?" he asks on the song’s opening verse, which, like the song itself, is a reference to his status as a minted legend. As further proof that Jay wasn’t standing in the way of any up-and-coming artists, he brought Cudi out to perform "Already Home" at his famed "Answer the Call" concert, which was held at Madison Square Garden on Sept. 11, 2009. The appearance gave Kid Cudi a promotional boost days before the release of his debut album, Man on the Moon: The End of Day. An album that fused hip-hop and indie rock, it drew two different crowds, sold 104,000 copies its first week, and helped signal a change of direction in the genre. A change that was further facilitated by another guest on the The Blueprint 3: Drake.

After earning critical acclaim and dominating radio, house parties, and clubs with tracks from his breakthrough project, So Far Gone, the Canadian anomaly had become rap’s biggest commodity. He provided the chorus to "Off That," a song about leaving the past behind in favor of all-new everything. Despite the song being one of the weakest on the project, it was a fitting placement for Drake. In a post-808s and Heartbreak era, a growing contingent of fans were tiring of the superthug persona and searching for music that precisely channeled their perspectives. Drake provided that, offering something which was "off that," so to speak. "That," in this case, being everything that was previously commonplace in hip-hop. The willingness to share his vulnerabilities—which, to this day, makes the insecure look at him funny—is what endeared him to the masses.

Throughout 2009, Drake proved that he had a penchant for crafting exceptional hooks. The chorus to "Fear" was especially piercing, as his repetition of "please don’t be scared of me" worked on two levels. Not only was he urging friends and family not to fear the celebrity that he was struggling to deal with, it was also a message to the hip-hop community: Don’t be alarmed by the change he signaled. Drake, along with Kid Cudi, is responsible for the redefinition of masculinity in hip-hop, which was traditionally drenched in bravado. Though he does plenty of posturing, he’s honest about what hurts him in ways that other rappers were simply afraid to be in the past.

November 2009 saw Drake, Kid Cudi, and Wale honored in GQ’s "Man of the Year" issue. They were ironically crowned the "Gangster Killers of the Year" since they were the exact opposite. "Wale is as famous for his live shows as for the slick-witted lyricism of his debut, Attention Deficit," Will Welch wrote. "Kid Cudi is the cutup who scored with the stoner anthem 'Day N Nite' and his album Man on the Moon. And then there’s Drake, who found himself turning down multimillion-dollar offers after his single 'Best I Ever Had' exploded." The GQ mention was a crossover springboard for the trio, particularly Wale, whose debut album was released around the same time. Unfortunately, the extra push didn’t help.

Despite receiving favorable reviews, Attention Deficit was a commercial failure, selling just over 28,000 copies during its first week. The fact that there was substantial buzz surrounding the album, as well as Wale’s inclusion on the roster for Jay Z’s Blueprint 3 tour and performance with the house band at the 2009 MTV Video Music Awards made the sales even more underwhelming. What’s more, the pairing of him and Lady Gaga on the album’s awkward lead single, "Chillin," failed to resonate. But, as his former manager Dan Weisman told XXL when the first week numbers returned, it was difficult to even find the album when it was released because stores were provided with a limited number of copies.

"Wale’s the type of artist who is bigger than the metrics [radio says] he is," Weisman explained. "That puts the label in a tough position in terms of physical distribution, and because of Twitter we are able to hear direct feedback from the fans about the problems they had actually finding the CD. But 64 percent of Wale’s sales came from digital outlets, which makes sense for Wale." That didn’t stop the jokes and talk of him being a bust from mounting, as Wale became the first member of the lauded new breed of rappers to face the industry’s ugly side. Fortunately, the commercial success Wale longed for arrived after he parted ways with Interscope.

Meanwhile, another rapper who would later achieve immediate success with Interscope was laying the foundation for future success without anyone paying attention.

A largely unknown Compton rapper named Kendrick Lamar released the Kendrick Lamar EP on the final day of the decade. Dropping his previous stage name, K-Dot, Lamar reintroduced himself to the world. Within less than a year, he would be dubbed hip-hop’s next great attraction. But, as he revealed on the EP’s opening track, "Is It Love, " his ascent was a long time coming.

"I used to write rhymes all day and all night/When y’all was playin’ Playstation, my pencils was erasin’ lines my conscious only knew was half tight/At 3:14 it’s time to get me a slice, my nigga," he rhymes over a haunting Angela McCluskey sample. The final proof that the last quarter of 2009 was a captivating time for hip-hop lies in the fact that its most cerebral artist, the purest lyricist to emerge in two decades, and the possibly best rapper of the moment (depending on your perspective) submitted a strong project that still got little recognition because it dropped while the majority of the world was getting drunk. Five years later, everyone knows his name.

In retrospect, what makes a period in music great is obviously what happened, but also what those events mean on a larger scale. Looking back, The Blueprint 3 was Jay Z’s way of giving younger artists the platform to succeed without completely fading to black. He continued this effort by inviting some of them to tag along on his Blueprint 3 tour that fall. Furthermore, many of these artists who began to gain traction during this time are among the most popular in hip-hop today. Kid Cudi, J. Cole, Drake, Wale, and Kendrick Lamar are all Grammy nominees, while Lamar and Drake—who were the least celebrated when they initially entered the game—are at the head of rap’s race in 2014. Moreover, the fall of 2009 included several unforeseen moments, from the quality of Raekwon's Only Built 4 Cuban Linx….Pt. ll to Shyne being released from prison, to Jay Electronica releasing one song so good that it’s kept the hip-hop community playing Where’s Waldo? with him five years later.

If nothing else, the fourth quarter of 2009 was a crystal ball: a preview of what was to come in the next decade. All that has transpired in hip-hop over the last five years simply makes looking at this moment in history more enjoyable and rewarding. It’s a reminder to absorb what’s going on around you, as it’s likely to indicate what’s about to happen next.

Julian Kimble has been chasing the feeling of fall 2009 since New Year’s Day 2010. Follow him on Twitter here.