You Won't Believe What Happened To The 2009 XXL Freshmen – It's Absolutely Devastating!

What happened to the 2009 XXL Freshmen? The answer might shock you. For every artist who parlayed that coveted cover spot into a lasting legacy, there’s another whose star dimmed just as quickly as it burned bright. The 2009 class entered the hip-hop world at a pivotal moment, armed with mixtapes, blogs, and a new digital playbook. But nearly fifteen years later, the outcomes are a stark, often devastating, lesson in the volatility of fame. From chart-dominating superstars to cautionary tales, we’re breaking down the complete trajectory of every rapper who graced that legendary list. The paths they’ve taken reveal as much about the industry’s brutal evolution as they do about the artists themselves.

The XXL Freshmen cover is more than just a magazine feature; it’s a cultural seal of approval, a prophecy of potential. For the 2009 class, the pressure was immense. They stepped onto the stage during a transitional era, where the internet was beginning to dismantle traditional gatekeepers. This group didn’t just benefit from the hype—they helped define the sound and strategy of a new decade. Yet, the very tools that launched them—social media, free music, viral buzz—also created a landscape where relevance is fleeting and missteps are permanent. Revisiting this roster isn't just an exercise in nostalgia; it's a forensic analysis of what it takes to survive in modern hip-hop.

The 2009 Hip-Hop Renaissance: A Perfect Storm for New Talent

To understand the 2009 XXL Freshmen, you must first understand the world they entered. Hip-hop in 2009 was at a cultural crossroads. The dominant sounds were splintering. On one side, the "backpacker" ethos—lyrical complexity, boom-bap production, and conscious themes—was experiencing a full-scale resurgence. On the other, the infectious, synth-driven club rap of the late 2000s was peaking. This tension created a wide aperture for new artists. The genre was hungry for fresh voices, and the method of breaking through had fundamentally shifted.

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Gone were the days when a major label co-sign was the only path. Lucky for them, the culture was experiencing a new wave of artists flooding the game through an entirely new method of breaking in. The rise of blogs like 2DopeBoyz and Nah Right, the omnipresence of YouTube, and the power of platforms like DatPiff for free mixtapes democratized access. An artist in a bedroom could build a national following without a single radio spin. The 2009 Freshmen were among the first generation to fully leverage this digital toolkit. They weren't just rappers; they were brands, content creators, and community builders from day one. This new paradigm lowered the barrier to entry but raised the bar for sustained success, requiring constant output, engagement, and adaptability.

The 2009 XXL Freshmen Roster: Stars of Tomorrow

The 2009 list was a eclectic mix that reflected the era's diversity. It wasn't a monolithic sound but a snapshot of hip-hop's expanding possibilities. The class included:

• Wale: The lyrical wordsmith from Washington, D.C., with a knack for clever punchlines and a dedicated fanbase.
• Ace Hood: The aggressive, technically proficient spitter from Florida, representing the raw energy of the streets.
• Kid Cudi: The introspective, melodic innovator from Ohio who blurred the lines between rap, rock, and soul.
• B.o.B: The genre-bending Atlanta talent who seamlessly fused rap with pop, rock, and electronic sensibilities.
• Charles Hamilton: The prolific, blog-era darling from Harlem known for his sheer volume of music and Sonic the Hedgehog-inspired persona.
• Asher Roth: The affable, white rapper from Pennsylvania who captured a specific college-student vibe with his breakout hit.
• Cory Gunz: The son of rap legend Peter Gunz, carrying the torch of New York’s lyrical tradition with a youthful flair.
• Blu: The soulful, jazzy lyricist from California, a critical darling in the underground circuit.
• Chiddy Bang: The Philadelphia duo (Chidera "Chiddy" Anamege and Noah "Break Science" Beresin) known for their upbeat, sample-heavy, party rap.
• The Cool Kids: The Chicago duo (Evan "Chuck Inglish" Ingersoll and Antoine "Mikey Rocks" Reed) with a retro, laid-back style and sharp fashion sense.

Each arrived with a unique story, a buzzing mixtape, and the weight of expectation. We're here to breakdown and look back the XXL freshman list and we start off with the 2009 list, a group that promised to shape the next decade. The question that followed them, and us, for years has been: We now look back at these artist and see where the promise led.

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Where Are They Now? The Fate of the 2009 Class

Wale: The Consistent Craftsman

Wale’s hustle hasn’t gone unnoticed, and his journey is perhaps the most straightforward success story of the class. He leveraged his XXL co-sign into a major label deal with Interscope. His debut, Attention Deficit (2009), was a critical favorite, showcasing his sharp lyricism over eclectic production. The 2011 hit "Lotus Flower Bomb" featuring Miguel became his signature song, earning a Grammy nomination and cementing his status.

After navigating label politics and a publicized feud with Drake, Wale took control of his career. He launched the highly successful Folarin mixtape series independently and later released a string of well-received albums like The Album About Nothing (2015) and Wow... That's Crazy (2019). He’s maintained a consistent output, a loyal fanbase ("The Board of Administration"), and diversified into podcasting (The Curious Case of...). While he hasn't achieved the superstar status of a Drake or Kendrick, Wale has built a durable, respectable career defined by artistic integrity and business savvy. He is the blueprint for turning a Freshman spot into a long-term, self-sustaining brand.

Attribute	Details
Real Name	Olubowale Victor Akintimehin
Born	September 7, 1984
Origin	Washington, D.C.
2009 Breakout	Attention Deficit album, "Chillin'" featuring Lady Gaga
Key Projects	The Album About Nothing, Folarin mixtape series
Current Status	Independent artist, consistent touring, successful podcast host

Ace Hood: The Underrated Powerhouse

Ace Hood arrived with relentless energy and impeccable technical skill. His 2009 mixtape Gutta and subsequent album Ruthless (2009) established him as a force in the trap subgenre. For years, he was a critical favorite for his sheer lyrical dexterity and aggressive flow, often compared to a young Lil Wayne. He scored several minor hits ("Hustle Hard," "Bugatti") but never broke into the mainstream upper echelon.

His career has been a study in consistent, high-quality output without a massive commercial peak. After leaving his major label, he thrived as an independent artist, releasing projects like Mr. Hood (2020) that delighted his core fans. He’s also become a respected voice in the industry, often speaking on the business of music and the importance of ownership. Ace Hood’s story is one of resilience. He never got the "devastating" breakup narrative; instead, he carved out a sustainable niche, proving that influence and respect can be a form of success separate from chart dominance.

Kid Cudi: The Influential Icon

Kid Cudi’s impact cannot be overstated. His 2009 debut Man on the Moon: The End of Day was a seismic event, introducing a vulnerable, melodic, and psychedelic style that directly influenced a generation of artists (from Travis Scott to Juice WRLD). He wasn't just a rapper; he was a mood, a feeling, a pioneer of the emo-rap and alternative hip-hop movements.

After a turbulent period with label issues, substance abuse struggles, and a highly publicized feud with Kanye West, Cudi experienced a monumental resurgence. His feature on Kanye's "Ghost Town" (2018) marked a reconciliation, and his own Man on the Moon III: The Chosen (2020) debuted at #1. He now enjoys a revered, almost mythical status. He's a successful touring act, a key member of the Kids See Ghosts duo, and a cultural touchstone. His journey had devastating valleys, but his creative legacy is untouchable. He proved that true innovation can weather any storm.

B.o.B: The Meteoric Rise and Troubling Fall

B.o.B’s story is arguably the most devastating trajectory of the entire class. In 2010, he was on top of the world. His debut The Adventures of Bobby Ray was a multi-platinum smash, yielding the inescapable hits "Nothin' on You" (feat. Bruno Mars) and "Airplanes" (feat. Hayley Williams). He was a chart-topping, genre-blending superstar with massive appeal.

But the success was short-lived. Creative differences with his label, Grand Hustle, led to a contentious split. His subsequent albums, Strange Clouds (2012) and Underground Luxury (2013), underperformed. Then came a period of profound public struggle. B.o.B became a vocal proponent of flat-earth conspiracy theories and other fringe beliefs, alienating many fans and peers. His releases became sporadic and erratic, often self-funded and with minimal promotion. Once a surefire hitmaker, he became a cautionary tale about the perils of losing your creative support system and the fragility of mainstream relevance. His recent independent music finds a small, dedicated audience, but the chasm between his 2010 peak and today is vast and sobering.

Charles Hamilton: The Prodigal Son of the Blog Era

Charles Hamilton was the pure, uncut essence of the 2009 blog era. He released an astonishing 50+ projects in a few years, all for free, building a cult following through sheer volume and a distinctive, Sonic the Hedgehog-inspired sound. His talent was undeniable—a nimble flow and a knack for melodic, introspective beats. He seemed poised for a major label breakthrough after signing to Interscope.

Then, it all collapsed. In 2010, he was dropped by Interscope following a highly publicized, messy legal dispute with his former girlfriend and collaborator, Briana Latrise, which involved allegations of abuse and a very public breakdown. His career went into a deep hibernation. For years, he was a "what if" story. Recently, he has staged a quiet comeback, releasing new music on YouTube and SoundCloud to a small but loyal audience. His story is a tragic reminder of how quickly personal demons and industry politics can derail immense talent. The potential that seemed limitless in 2009 remains largely unfulfilled.

Asher Roth: The One-Hit Wonder

Asher Roth’s 2009 breakout "I Love College" was an anthem. It captured a specific, carefree moment in youth culture and made him a star overnight. His debut Asleep in the Bread Aisle (2009) was solid, but he was forever tied to that one mega-hit.

Attempts to evolve his sound away from the "college rap" tag were met with commercial indifference. He released a few more albums and mixtapes to diminishing returns. Unlike others who pivoted to independence, Roth largely receded from the mainstream spotlight. He’s occasionally resurfaced for viral moments or to reflect on his brief moment in the sun. His path is a classic one-hit-wonder narrative, highlighting the immense difficulty of escaping the shadow of your defining song, especially when that song defines a genre trend that quickly evolves.

Cory Gunz: The Son Who Forged His Own Path

Son of legendary rapper Peter Gunz, Cory arrived with a target on his back and a formidable skill set. His 2009 appearance on Lil Wayne's "6 Foot 7 Foot" was a massive co-sign. He had the technical ability and the name recognition. His 2011 single "Down" featuring Wiz Khalifa was a solid hit.

However, the shadow of his father and the high expectations proved difficult. His debut album Son of a Gun (2018) arrived after years of delays and independent grind. He never achieved the superstar status many predicted. Instead, he has maintained a steady career as a respected underground rapper and collaborator, often popping up on features. He hasn't had a "devastating" fall from grace, but the gulf between the predicted superstar and the respected journeyman is significant.

Blu: The Critic's Darling

Blu was the soulful, jazzy lyricist from Los Angeles who represented the conscious, alternative side of the Freshmen class. His 2007 mixtape Below the Heavens (with producer Exile) was already a cult classic. His inclusion on the 2009 list was a nod from the establishment to the underground.

Blu has never chased mainstream fame. He has released a prolific, sometimes bewildering, catalog of albums, mixtapes, and collaborations, often self-released or on small indie labels. Projects like Jesus (2011) and Good to Be Home (2014) are beloved by purists. He tours consistently to a dedicated fanbase. His path is the opposite of devastating—it's a triumph of artistic integrity over commercial ambition. He proved you could be a XXL Freshman and remain true to the most underground corners of the culture.

Chiddy Bang: The Duo That Fizzled

Chiddy Bang's 2009-2010 run was infectious. Their mixtape The Swelly Express and the hit single "Opposite of Adults" were everywhere, blending hip-hop with indie rock samples and an upbeat, party vibe. They seemed destined for pop-rap crossover success.

Their major label debut Breakfast (2012) underperformed. The duo quietly disbanded shortly after. Chidera Anamege (Chiddy) pursued a solo career and later became a media personality and entrepreneur, even setting a Guinness World Record for the longest freestyle. Noah Beresin (the producer) moved into production and DJing. Their story is a swift and quiet dissolution. The chemistry that worked on free mixtapes didn't translate to a sustained major label project, and the group vanished from the mainstream conversation almost as quickly as they arrived.

The Cool Kids: The Stylish Survivors

The Cool Kids brought a laid-back, retro-futuristic vibe and impeccable fashion sense. Their early mixtapes and the When Fish Ride Bicycles EP (2011) were critically adored. They were the hipster darlings of the rap world, with a sound that felt both nostalgic and new.

They faced lengthy delays for their debut album, which eventually came out in 2017 as Special Edition Grand Master Deluxe to positive reviews but little commercial splash. Both members have pursued solo projects—Mikey Rocks with his Rocks series and Chuck Inglish as a producer. They occasionally reunite for tours and features. Their journey is less about devastation and more about slow-burn, niche longevity. They never had a massive pop hit, but they’ve maintained their cool, cultivated a loyal fanbase, and remained respected figures in the style-conscious wing of hip-hop.

The Devastating Truth: What the 2009 Class Reveals About Hip-Hop's Volatility

Xxl gives an update on what the 2009 freshman class' been up to since gracing our cover two years ago. That update, now a decade old, tells a brutal story. The "devastation" isn't that every single artist failed—far from it. The devastation lies in the sheer unpredictability of it all. The same tools that democratized success—free music, social media, viral potential—also mean that a career can peak and plummet in the time it takes to release a mixtape. There is no safety net.

The class of 2009 saw:

• The Stratospheric Rise & Fall (B.o.B): A #1 hitmaker reduced to a niche independent artist with controversial views.
• The Prodigal Son's Return (Kid Cudi): A fall from grace so deep it seemed final, followed by a triumphant, label-backed comeback.
• The Consistent Craftsperson (Wale): A steady, label-supported climb to a sustainable, if not superstar, career.
• The Underground Saint (Blu): A deliberate rejection of the mainstream path in favor of pure artistic expression.
• The Lost Potential (Charles Hamilton): A talent whose personal and legal battles erased a seemingly inevitable rise.
• The Quiet Fade (Asher Roth, Chiddy Bang): Brief, bright flames that couldn't sustain momentum beyond their initial viral moment.

It’s been almost a year since we did the article on xxl’s “the 10 freshmen”—and in that time, the landscape has only grown more treacherous. Streaming payouts are minuscule, TikTok dictates trends in seconds, and the audience's attention span is shorter than a 30-second Instagram Reel. The 2009 class had the benefit of a slightly slower digital burn. Today's Freshmen face an even more volatile environment.

Lessons for Aspiring Artists: Beyond the Freshmen Cover

For every artist dreaming of that XXL cover, the 2009 class offers painful but invaluable lessons:

1. The Cover is a Starting Line, Not a Finish Line: The co-sign opens doors, but you must walk through them with a plan. Build a team you trust—managers, lawyers, producers—who have your long-term interests at heart. B.o.B's fallout with Grand Hustle is a textbook case of a broken artist-label relationship.
2. Diversify Your Brand Immediately: Don't just be a rapper. Be a content creator, a curator, a businessman. Wale’s foray into podcasting and consistent touring outside of album cycles is why he’s still here. Relying solely on music sales or streams is a fragile strategy.
3. Protect Your Mental and Financial Health: The stories of Charles Hamilton and B.o.B underscore how quickly personal turmoil and financial mismanagement can end a career. Own your masters when possible, budget for lean times, and prioritize your well-being. The grind is real, but burnout is permanent.
4. Authenticity is Your Strongest Asset, But It Has Limits: Kid Cudi’s vulnerability created a new lane. Asher Roth’s "college" persona became a cage. Find the core of your art that is truly unique and evolve it without abandoning it completely.
5. Community Over Clout: The most enduring artists from this class (Blu, The Cool Kids) maintained strong connections with their core fans and peers. They engaged in the culture, not just atop it. Nurture your dedicated fanbase; they will follow you through stylistic changes and industry shifts.

Conclusion: A Legacy of Sound and Silence

The 2009 XXL Freshmen class was a snapshot of hip-hop at a digital inflection point. They were the first to truly use the internet as a primary launchpad, and their collective story is the story of the modern music industry itself—glamorous, unpredictable, and often cruel. The Atlanta rapper’s hustle hasn’t gone unnoticed (B.o.B in his prime), and from Ace Hood to Wale, we've seen every possible outcome: sustained success, tragic fall, quiet perseverance, and legendary influence.

The "devastating" truth isn't that most of them aren't on the radio today. The devastation is in the lost potential, the voices silenced by their own demons or the industry's indifference, the sounds that could have evolved but were cut short. Yet, from this class, we also get hope. We see that a career can be rebuilt (Cudi), that integrity can be maintained (Blu), and that consistency can outlast hype (Wale).

With 2.8m subscribers in the hiphopheads community and countless forums and YouTube channels dedicated to these retrospectives, our fascination endures. We revisit these lists not just to grade the artists, but to understand the game itself. The 2009 Freshmen taught us that in hip-hop, there are no guarantees. The cover shines bright, but the light it casts can be a spotlight or a flare—beautiful to watch, but destined to fade. The real winners are those who learn to build their own light, long after the magazine has been folded and forgotten.