By the late 90s, Hip Hop had established itself as an industry powerhouse and a voice of authority and militance (see Jay Z’s 1999 boycott of the Grammy Awards).

Given the strength of its popularity, it was inevitable for more and more studios to crack up their wallets and roll out visuals to attract the fans who had no problems spending money on anything containing a mic, a durag or throwback jersey.

Much like the music of the decade, bad Hip Hop movies were churned out in droves and made a lot of money in the process, eventually watering down the quality of the overall product. Nonetheless, several gems managed to emerge from all the reel clutter, including a couple of flicks that produced a couple of Academy Awards for Best Original Song (that you’ll see down below).

Without further adieu, here are the best Hip Hop films of the 2000s.

How High (2001)

Director: Jesse Dylan

After the success of Friday, hood stoner movies were in abundance like the bootleg man himself. However, Method and Redman found a little something extra in their dime bag–literally, as the film depicted them as two hustler college students who got good grades by taking blunts to the dome. It usually works the opposite in real life.

Star Power: Method Man & Redman, Mike Epps, Tracy Morgan, Cypress Hill, Fred Willard, Essence Atkins, Lark Voorhies, Chuck Liddell

State Property (2002)

Director: Abdul Malik Abott

“Get down or lay down!” That was the popular catchphrase from Beanie Sigel’s “Beans” character as he portrayed a ghetto Tony Montana-type whose empire was sprawled all across Philly. Although the performances weren’t exactly Oscar-worthy, the film encompassed a natural aesthetic that made the entire script believable throughout. And Jay Z putting out hits in Pig Latin and Dame Dash playing a foot fetish-having ruthless kingpin is the hilarious kind of shit that we’ll never get again.

Star Power: Jay Z, Dame Dash, Beanie Sigel, Memphis Bleek and damn near the entire roster of Roc-A-Fella Records

Brown Sugar (2002)

Director: Rick Famuyiwa

Romantic comedies are often seen as cheesy and Hip Hop movies are often too brash for the average movie goer. Brown Sugar met both parties in the middle that was undeniably the perfect blend of sweet and street. Sanaa Lathan starring as XXL’s editor-in-chief, Taye Diggs dealing with culture-depreciating acts and Yasiin being too chickenshit to holla at Queen Latifah were only a few of the gems the movie packed on the surface. When did you fall in love with Hip Hop?

Star Power: Sanaa Lathan, Taye Diggs, Queen Latifah, Mos Def, Nicole Ari Parker, Boris Kodjoe, Wendell Pierce, Common, Talib Kweli, Kool G. Rap, Method Man, Angie Martinez, Russell & Kimora Lee Simmons, Slick Rick, Doug E. Fresh, Dana Dane, Black Thought, Questlove, Jermaine Dupri, Beanie Sigel, Big Daddy Kane, De La Soul, Pete Rock

Paid In Full (2002)

Director: Charles Stone III

The legacy of Rich Porter, Alpo Martinez and Azie “AZ Faison a.k.a. Rich & Po and AZ would go on to inspire Hip Hop music to no end (especially from eventual NYC rap legends) and Paid in Full, its loosely based biography on their rise to power during the late 80s still inspires DIY street pharmaceutical salesmen to this day. Fans of HBO’s The Wire would go on to appreciate the Roc-A-Fella film even more as a chunk of the cast propelled the story to hood rich greatness.

Star Power: Cam’ron, Wood Harris, Mekhi Phifer, Dame Dash, Angie Martinez, Regina Hall, Elise Neal, Jamie Hector, Hassan Johnson, Doug E. Fresh, Busy Bee, Chi McBride

8 Mile (2002)

Director: Curtis Hanson

At the time of 8 Mile’s release, Eminem was the biggest rapper on the planet but he still was barely removed from his humble beginnings, making his street cred just as alluring as his record sales. The film put a Hollywood spin on his biography without adding the gloss and immediately put Slim Shady in high demand to star in more movies (which, sadly never came into fruition). Yet it did help him earn an Academy Award for Best Original Song (“Lose Yourself”) and made a household name out of Mekhi Phifer.

Star Power: Eminem, Proof, Kim Basinger, Anthony Mackie, Mekhi Phifer, Brittany Murphy, Xzibit, Taryn Manning, Brandon T. Jackson, Sara Stokes

Freestyle: The Art Of Rhyme

Director: Henry Alex Rubin

Capitalism eventually made the rapper the forefront of Hip Hop once the culture’s economics became more noticeable. Freestyle: The Art Of Rhyme focuses specifically on freestyling and the many subcultures that emerged from that including the battle rap scene. The Henry Alex Rubin directed documentary exists in a world where emcees like Aceyalone, Supernatural and others are the kings of improvisational rhyming.

Star Power: Mos Def, The Roots, Pharoahe Monch, Planet Asia, Sway

Hustle & Flow (2005)

Director: Craig Brewer

Hustle & Flow could be somewhat be considered the Southern Hip Hop cousin of 8 Mile. It also transformed Terrence Howard and Taraji P. Henson into award-winning caliber thespians before the days of Lucious and Cookie. The real story would come through Three 6 Mafia winning an Oscar for “It’s Hard Out Here For A Pimp” which was performed with a real rap swagger from Howard himself.

Star Power: Terrence Howard, Ludacris, Taraji P. Henson, Anthony Anderson, Juicy J & DJ Paul, Taryn Manning, Elise Neal, Haystack, Isaac Hayes

Get Rich Or Die Tryin’ (2005)

Director: Jim Sheridan

50 Cent’s popularity was at a fever pitch in 2005. The Massacre was the biggest selling album in rap that year and G-G-G-G-Unit’s brand became big enough to even have a video game loosely based on his life through Bulletproof. Getting In America director Jim Sheridan for the fictional cinematic adaptation of his life Get Rich Or Die Tryin’ was an inspired move to really make a film that didn’t feel too much like another cash grab. (8 Mile comparisons aside.)

Star Power: 50 Cent, Terrence Howard, Viola Davis, Joy Bryant, Leon, Mykelti Williamson

ATL (2006)

Director: Chris Robinson

Like they’ve always down when their region was neglected, the South banded together to offer up its official coming-of-age story with ATL. Robinson, previously known for his benchmark Hip Hop videos, assumed the role of director as both Outkast’s “Southernplayalistic” back roads and T.I.’s trap alleyways were mashed together with glimpses from Georgia suburbia life to fully envision the perspective. Producers Dallas Austin, Tionne “T-Boz” Watkins, James Lassiter and the only and only Will Smith did a bang-up job of rounding out the reel and Big Boi’s uncharacteristic performance as the bad guy and the introduction of Lauren London to salivating boys nationwide also packed on to the film’s legacy. T.I.’s 2006, platinum album, King, also served as the film’s unofficial soundtrack. Talks of a sequel are now currently in the works.

Star Power: T.I., Big Boi, Lauren London, Killer Mike, Keith David, Evan Ross, Tasha Smith, Jason Weaver, Mykelti Williamson, Monica, Jazze Pha, Bone Crusher, Malika and Khadijah Haaq

This Is The Life (2008)

Director: Ava Duvernay

Once on Twitter, Ava Duvernay equated her relationship with Hip Hop to being in an abusive relationship due to rampant misogyny and violence against women. By that time, she had scored high praises for her Martin Luther King mini-biopic, Selma. Going back to her directorial debut This Is the Life, she gives history into Los Angeles’ alternative Hip Hop scene through the eyes of eatery and open mic platform, the Good Life Cafe. Those more interested in Freestyle Fellowship than Death Row should have much to be entertained by.

Star Power: Ava Duvernay, Busdriver, Medusa, Abstract Rude, Charlie 2na, Aceyalone