Sean Penn acting pretty Gangsta in Gangster Squad
Sean Penn acting pretty Gangsta in Gangster Squad

Tommy Gun Tunes: A Playlist for Gangstas and Gangsters

Today, the highly anticipated gangster movie Gangster Squad hits theaters. The film, which will hopefully usher in a resurgence in classic gangster period pieces, promises that classic shoot 'em up action with a sleek new style. Of course, in honor of the occasion, we at the Weekly feel compelled to drop some gangsta shit! So, to prep you gangsters and gangstettes on the way to the theater, here's our official Gangster Playlist.

50 Cent - "What Up Gangsta?"2003

The rise of 50 Cent a decade ago was a magical time for that true gangsta feeling to return to the rap world in a bold new way. The release of his major label debut

Get Rich or Die Trying

was nothing short of an event, and one of gangsta rap's biggest moments of the decade. What better way to set the tone and start off our playlist than with "What Up Gangsta?," a song so infectious, it's masterful hook became a hip-hop catchphrase without the song even being released as a single. That's gangsta.

Coolio - "Gangsta's Paradise"1995

A learning institution may not be the most gangsta of places, but when you're gangsta enough to make a post-

Batman Returns

Michelle Pfeiffer walk down your high school to find out what you're up to, you've hit the pinnacle of 1995 coolness. Naturally, this described Coolio and the video for the

Dangerous Minds

soundtrack's "Gangsta's Paradise." Who would have guessed that within one year Coolio would maintain the same artistic credibility while doing songs for Nickelodeon. That's gangsta.

Geto Boys - "Damn it Feels Good to be a Gangsta"1992

Speaking of movies, how gangsta was director Mike Judge for making the bonus track from the first Geto Boys

Greatest Hits

album a cult phenomenon by featuring it prominently in his 1999 classic

Office Space

. Along with unforgettable verses, and a beat whose drums knock with the absolute best, its placement within the film has resonated with viewers in a way to even occupy a spot in the heart of the rare "I hate all rap music except..." contingent. Judge would continue to implement the Geto Boys by giving member Scarface an absolutely stellar cameo and post-credits scene in his follow-up film


. That's gangsta.

Steve Miller Band - "The Joker"1973

Steve Miller may not strike many as being particularly gangsta, but when you can sneak entirely made up words like "pompatus of love" into the American lexicon for 40 years, that had to count for something. Odd as it is, "The Joker" is a largely self-referential song whose legacy has out grown each of the other Miller songs it mentions. It was also used to create one of the most shocking and endlessly entertaining Geto Boys songs

"Gangsta of Love."

That's gangsta.

Outkast featuring Slimm Calhoun, BlackOwned C-Bone and T-Mo - "Gangsta Shit"2000



, really the last proper Outkast album, featuring the duo working together at the height of their critical acclaim, creative inventiveness and commercial resources, it shouldn't be surprising that there's a few different versions of "Gangsta Shit" floating around. While we've chosen the album version, being the perfect hybrid of smooth laidback funk traditionalism with that progressive Dungeon Family arrangement, the various mixes in circulation show how nuanced every aspect of Outkast's music at the time truly was. That's gangsta.

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