XXL's Most Promising Class: Revisiting the 2009 Freshmen, Pt. 2

We continue our deep-dive into the iconic '09 XXL Freshmen Class.
Publish date:
Social count:
We continue our deep-dive into the iconic '09 XXL Freshmen Class.

Welcome to Part 2 of our look at the past and present of the storied '09 XXL Freshmen Class cover. If you haven't yet, catch up on Part 1 here.


Blu, the mighty Blu, a talent that arrived like a ray of sunshine when so many considered rap on life support. In 2007, Below The Heavens put Blu on a pedestal as a savior, someone who had the prowess to make rap great again. Below The Heavens paired breathtaking lyricism and soulful production, the kind of project that changes how you view the standard of top-tier rap. Acclaim surrounded him, the internet saw a champion in Blu and becoming an XXL Freshman two years later only further increased the hope that he would take his talents to rap’s mountaintop. If there was a stairwell that led to hip-hop's heaven, Blu was taking the steps and we cheered for his progress. 

Despite all his talent, the stars never aligned for Blu in the commercial sense. When Warner Bros. dropped him in 2011, blaming him for an album that lacked songs that could crossover, the need for a record for radio ruined his big moment. What was once a hopeful major label debut in the making turned out to be years of toiling that lead to nothing but time he couldn't get back. Time can be the difference between breaking through the glass ceiling and being trapped in the basement. Without the majors backing Blu’s album, it failed to reach the masses.

Albums like York, Good To Be Home and Bad Neighbor (with MED and Madlib) were met with rave reviews, but they all arrived long after the height of Blu’s buzz.

More recently, Blu has openly struggled with mental health issues. The fight against the music industry was nothing like the fight within himself. From the outside looking in, his health appears to be improving—this year he actually dropped four collaborative projects—but only Blu knows for certain if better days are ahead. It's so sad to see such a talent not be recognized for being exceptional, but the game isn't kind, even to a genius such as Blu. 

Charles Hamilton

Charles Hamilton was special. Rap doesn’t always embrace what’s different, and Charles was in a world of his own. He saw Sonic The Hedgehog as a deity, he constantly expressed the notation that God was a woman and he blogged his every thought, idea and theory for the world to read. He was different, eccentric, but the passion he had for rap could be felt within his every bar. The kind of lyricist that poured his life into the pen, and mixed his reality with metaphors, similes, and punchlines.

He created in excess, self-production meant he never ran out of sounds to rap upon. Think of Lil Wayne’s leak period except all the music came out intentionally. The Hamiltonization Process was a streak of full-length original music releases. Before FutureHive, there were the Starchasers. Charles built a fanbase like no other, the Starchasers were a cult that felt deeply connected to the rapper, and by being brutally honest about his struggles, he became a voice that assisted many with their own problems. The song “Brooklyn Girls,” his magnum opus The Pink Lavalamp, and a deal with Interscope is the trifecta that led to him arriving on the Freshmen cover. As a ruler of the internet, a talented wordsmith and a promising producer, everything pointed to Hamilton being a success.

Slowly, and sadly, it all began to unravel, the downward spiral of his fall. There were small signs, but the final straw was crediting J Dilla as the executive producer of his album—and not in the abstract sense. Charles promoted this idea that the spirit of J Dilla came from the other side to assist with his project. What Dilla means to the hip-hop community is deeper than music, and by crossing that line, he crossed into waters where the sharks lacked empathy and only wanted blood. He was dropped from Interscope before his major label album could be debuted. His struggles with drugs and issues with mental health escalated, and soon he was just a sad sight to see.

The rough years are behind him now, and Charles has been steadily working on his return. Earlier this month, he released Hamilton, Charles through Republic Records, finally an album pushed through a major. This year also saw Red Bull Academy doing a full-length documentary on his life (with a brief cameo of the old DJBooth office), giving a deeper look on his brilliant, yet troubled, creative mind and all the darkness in his life. Out of all the freshmen, he was the first to fall, but let his perseverance serve as inspiration that it’s never too late to get back on your feet. May his life move forward with a bit more mercy and kindness.

Mickey Factz

Mickey Factz cared about lyricism. From law school to the recording booth, Mickey came into the game bringing a poet’s prowess over N.E.R.D. production. Freestyling over the classic In Search Of... instrumentals sparked the first wave of onlookers, listeners who were impressed by his skills. He continued to build a following by demolishing records as if there was actual poison in the lead of his pen. More than just an emcee, Mickey could create concepts and write songs that went deeper than just barraging bars. Skill and consistency unlocked the doors for Mickey to walk into the major leagues. XXL saw promise, and so did Jive Records, who signed him to a major label contract in 2010. The Achievement was the slated title for his major label debut—there was a lot of hope surrounding the album and the future of the emcee. 

Mickey had the commercial with Honda, had music in the video game Fight Night, was revered by Lupe Fiasco and respected by fellow wordsmiths alike. Anyone watching his career could see The Achievement was leading up to a breakthrough. Sadly, with each release date came another push back. With each new mixtape that served as an apology for the delay, the wait grew longer. The conceptual Mickey MauSe mixtape, released in 2012, was met with the highest praise for his incredible storytelling and inventive execution, but it failed to explode beyond the underground. A label had caused another artist to miss their opportunity to capitalize on all the excitement around them.

Mickey never gave up on The Achievement, an album that he was finally album to deliver earlier this year. For a project six years in the making, there's a reason to celebrate the liberation of another long-awaited hip-hop album. Along with the project, Mickey went on a tirade across radio shows still displaying a pen with a potency that Frank Lucas would admire. Super Saiyan Mickey has yet to lose it.


Wale on the cover of XXL was a statement—someone is making noise in the DMV that you have to hear. A region that wasn’t known for blossoming new rap talent had a face, an emcee that could mix superb wordplay with infectious go-go flavor. Home embraced him first, but the internet allowed him to expand beyond his city and start to touch the masses. It all started with the 100 Miles & Running mixtape, and from there every step just took him higher. With a fashion-forward flyness and talent as a writer, Wale was seen as the cool backpacker that could go major. Interscope got him early, I remember nothing but sheer excitement surrounding his forthcoming debut.

Wale faced the tragedy of undershipment, the low sales championed him a flop, and soon the promising lyricist was without a label despite favorable reviews. He was the first rapper to bring Lady Gaga into hip-hop, but it didn’t cross over.

From then on Wale’s career would be a series of incredible highs and lows, but he is without question one of the two most commercially successful artists on this list. Among his many accolades are two No. 1 albums, two albums certified Gold, two singles certified Platinum, and two singles certified Gold.

Wale went from stumbling to soaring with the smoothness of a moonwalk across a waxed floor. His career is one that’s had rocky moments, but XXL was correct in their prediction that he would go far. Rick Ross also foresaw a bright future for him when signing Wale to MMG. Surviving in the game this long is tough, but Wale has proven he belongs. He may believe he is underrated, but such a career should be celebrated. 

Kid Cudi

Last, but certainly not least, Kid Cudi. The man who left Cleveland for New York. The man who gave Kanye the blueprint for his most genre-shifting album. “Day 'N' Night” was big, an inescapable single, there was no denying that he was going to be a polarizing artist in the future. I'm still baffled they allowed him to complete his

I'm still baffled they allowed him to complete his XXL freestyle with a wrap around his face, but it was fitting given his unconventional style. Cudi never tried to be your traditional rapper, his music came from a different place, and it’s a big reason why he saw success, and so quickly. It was different—dark and personal. If Drake wore his heart on his sleeve, Cudi wore his soul like a crown. You couldn’t have Cudi without the demons.

Cudi will go down in history for being a game changer and genre-shifter. He ushered in an age, birthed artists, and altered the sound. There was no name for his fans, not one that I can recall, but he had a similar effect as Charles—people admired Cudi as a big brother figure, more so than a rap artist. He is still daring, outspoken, occasionally obnoxious, and an off-putting asshole, but ultimately being his fervent self. Cudi cares about art, even when musically he has failed to ascend beyond his prime. The best days feel behind him, but he’s still daring enough to try, even when the idea is much better than the execution. Years later, Cudi is still here, so are his demons, and we still watch because he has never ceased to be polarizing. May he find peace one day. 

When it’s all said and done, I’ll always look back on the ‘09 Freshmen Class as the best that XXL ever selected. At the time it seemed that the selections were truly based on who had the potential to be the bright stars of tomorrow, despite what the future brought.

The biggest lesson is that there’s no telling what tomorrow will hold. We have hope, just like our parents did the day we graduated. This is a hope we will continue to share as new artists enter hip-hop with the twinkle of a star in the making.


By Yoh, aka '09 Yoh, aka @Yoh31

Photo Credit: XXL