The 50 Greatest Bay Area Rap Songs

Too Short, E-40, Mac Dre, Luniz, and 2Pac are just a few of the great artists you'll find on our list.

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The Bay Area has a chip on its shoulder when it comes to hip-hop. Everyone steals Bay Area slang, but the radio won't play Bay Area music. It doesn't help that The Bay's artists never want to deal with major labels, and then cry foul when they don't get spins any further east than Sacramento.

This relative isolation has led to a certain kind of creativity, or strangeness, depending on how one sees it. Whether it's E-40's "Woody Woodpecker on crack" voice, Keak da Sneak's smoker's cough gibberish, Mac Dre's ecstasy-twisted dance moves, or Andre Nickatina's apparent obsession with Jungle Book, some of the Bay Area's most celebrated artists are downright bizarre—and that's what people love about them.

This alternative approach to rap, in the East Bay especially, has a long tradition outside of street rap, that goes back to Digital Underground, Hieroglyphics, Hobo Junction, and continues today with internet phenomenon Lil B. In the Bay Area, gangsta rap is not all that serious, and serious rap is still really fun.

Would the Bay Area give up its strangeness for a shot at the mainstream? We hope not. In any case, here's a primer with The 50 Greatest Bay Area Rap Songs for those who have been missing out. Don't be surprised if you feel like you really missed out; you did.

Listen to Complex's Best Bay Area Rap Songs playlists here: YouTube/Spotify/Rdio

Written By Willy Staley (@bushwickwill)

50. N2DEEP "Back to the Hotel"

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You'll recognize the same horn sample that would later be sampled by Wreckx-N-Effect for "Rump Shaker" and Ice Cube for "Friday." N2Deep, a stone-faced Latino duo from Vallejo, were the first to use the sample from Lafayette Afro Rock Band's "Darkest Light." This song is notable for its prominent use of a bizarre piece of early '90s West Coast slang: cock, meaning vagina. The second verse ends with TL saying "back to the telly, I gotta get some new cock," followed by echoes of "new cock" over and over again, into the bridge. That did not age well.

49. MC Hammer "U Can't Touch This"

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Hammer's legacy has become a bit of a punchline these days, but there's no denying that he was on top of the rap world when he took over the pop charts with "U Can't Touch This." Rapping over a funky sample from Rick James' "Super Freak," everything from the huge pants he wore in the video to catchphrases like "You can't touch this" and "Stop... Hammer time!" became huge pop culture references. The song also helped Hammer sell 18 million units&#8212and gave him the financial resources to start spending like a madman. Unfortunately, Rick James sued, got a profit-sharing settlement out of court, and Hammer eventually went broke trying to support a payroll the size of an NFL starting roster. But that doesn't dampen the impact that this song had in softening the opposition of mainstream America to rap.

48. The Team "Bottles Up"

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The Team, comprised of Clyde Carson, Kaz Kyzah, and Mayne Mannish, made some of the best radio- and club-friendly hyphy music back in the days when it would be acceptable to do so. It provides a nice time capsule of what could have been, had Bay Area rap blown up to be as big as people thought it would, back in the middle of the last decade. Here they tone down the ecstasy references, and made a drinking song instead, which would certainly be more acceptable to a nationwide audience. Strangely, The Team shouts out Taaka vodka&#8212as in, "we put the aaahh in vodkaaahhhh", which they don't—in addition to other, higher-shelf liquors.

47. E-40 f/ Keak da Sneak "Tell Me When to Go"

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This was mainstream America's first taste of what was going on in the Bay Area around 2005. Over a strangely not-very-hyphy Lil Jon beat—who, it goes without saying, is not from the Bay Area—two of the Bay Area's most distinctive voices attempt to break it down for a wider audience. E-40's call-and-response section is practically a checklist of Things That Are Hyphy, presumably there for didactic purposes. The song is fun, for sure, but it's also very calculated and clearly curated by a major label.

46. The Conscious Daughters "Fonky Expedition"

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The Bay Area doesn't make it easy for female MCs, which makes The Conscious Daughters that much more impressive. "Fonky Expedition" goes to show that the girls can roll hundred spokes and swing figure-eights with the fellas&#8212and, more importantly, that they can provide the soundtrack for it.</p>

45. B-Legit f/ Levitti "City To City"

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E-40 is one of rap's best nepotists. His group, The Click, was composed of 40, his sister Suga-T, his brother D-Shot, and his cousin B-Legit. He would later go on to sign his nephew Turf Talk, and his son, Droop-E. However, contrary to conventional wisdom, 40's mix of business with family would prove quite fruitful; everyone in his family is really good at rap, especially B-Legit. B-Legit the Savage was better known for his hard-hitting Mobb music raps, but this radio-friendly number with vocals from Sic-Wid-It's in-house R&B vocalist, Levitti, is enough to tame the savage in all of us. Break out the Carlo Rossi Rhine—never the Chablis!&#8212and the bubble bath for this one. </p>

44. Husalah "Sleep With the Fishes (Boom Clack)"

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Over a beat that could easily be described as postmodern, or perhaps self-referential, for its use of what sounds like a trunk rattling, and a person saying "boom clack," Husalah does what he does best: talk shit, sing, and borrow rhymes from Too $hort classics. While not typical of many other darker, more thoughtful Hus tracks, "Sleep Wit Da Fishes" is a great example of the energy and exuberance&#8212and absurdity&#8212that Husalah brings to the table.</p>

43. Spice 1 "187 Proof"

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This song features one of the most famous opening couplets in Bay Area rap history. Also, it is perhaps the earliest instance of a crime story told with brand names as stand-ins for actual names; many other rappers would go on to imitate this type of story-telling technique, but none ever did it as well as Spice 1, who followed this alcohol crime story up with "187 Pure," which recounts the misadventures of Indo Weed, Dank, and a man named Coke who carries a cane. For "187 Proof," Spice's story-telling was visualized with the single best stop-motion rap video ever made. If you have ever wanted to see booze bottles shoot at one another, or wondered what sort of creative issues you might run into attempting to depict a wino who is also a bottle of wine, it's really worth a watch.

42. Saafir "Light Sleeper"

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Saafir, of Oakland's Hobo Junction crew, free associates over a dreamy, almost ambient beat. While other rappers from Oakland were talking about the amount of pussy they were getting, Saafizzle was thinking about the multitudes of personae contained within his head. The video for this song has some hilariously janky use of early green screen technology.

41. San Quinn "Shock the Party"

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Easily one of the Fillmore District's most widely-respected voices, and one its most prolific, San Quinn has been making music since he was a teenager, and continues to do so today. In a city not known for deft lyricists, San Quinn stands out. "Shock the Party" is full of complex rhyme schemes over a classically mobbed-out JT beat, perfect for getting low to; this was long before the Bay Area became known for its funny dancing, but San Quinn's crew, the Get Low Playaz, were known for "getting low"—walking around in a crouch while popping your collar, with both hands. It looks hilarious.

40. Too $hort "Blow The Whistle"

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Okay, Lil Jon is capable of making a good hyphy beat. He managed to make a gray-whiskered Too $hort sound pretty damn young on this track, even as he runs down his extensive resume, and takes credit for making the word "bitch" popular&#8212ask Dave Chapelle. This beat would become even more popular a couple years later, due to its use of a referee's whistle, when Jay-Z dissed Deshawn Stevenson over it, in retaliation for Deshawn's disparaging comments about LeBron James. Not that Hov was the first to engage in an inter-disciplinary beef with an athlete; that would be E-40, who decimated Rasheed Wallace on 1996's "Record Haters."

39. E-40 f/ Spice 1, 2Pac & Mac Mall "Dusted and Disgusted"

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Virtually every classic Bay Area rap album has a superb posse cut; there are few lone wolfs in the Bay. On In a Major Way, 40 Water invited East Bay legends Mac Mall, Spice 1, and 2Pac to help him tell a sinister tale of revenge, cold-hearted bitches, and slu-uh-slu-uh-slugs. While Tupac came up in the Bay Area, between Marin City (as in, Marin County) and Oakland, he spent so much of his career in Los Angeles that it's easy to forget he was a Bay Area dude. In fact, if you watch the video version, Tupac's verse is replaced by one from Celly Cel, presumably because Pac was locked up at the time. Goes to show, you don't know what you got 'til it's gone.

38. IMP f/ Cellski, Dre Dog & Chuey "Frisco"

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Another posse cut, this time on the nicer side of the Bay, San Francisco. The Ill Mannered Posse (Cougnut and C-Fresh), out of SF's Lakeview neighborhood, released two of the most slept-on early '90s gangsta rap albums of all time, 1993's Back in the Days and 1995's Ill Mannered Players. This ode to the City by the Bay includes fellow Lakeview residents Cellski and Chuey, as well as Filmore's Dre Dog. You might think it doesn't include any rappers from Sunnydale because of the long-standing beef between Lakeview and the Swampy D, but it's actually because there are no good rappers from Sunnydale. Sorry.

37. "11/5" "Killahoe"

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Bay Area rap has never been known for being fair to the fairer sex. This song is no exception, though it should be noted that 11/5, from SF's Hunters Point, doesn't mean it in the literal sense. This, like Captain Save-a-hoe, is just one of those phrases that stuck around in Bay Area rap longer than anyone would have guessed. Gloria Steinem would probably sing along with that hook, it's so catchy.

36. The Coup "Fat Cats, Bigga Fish"

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Oakland Marxist-rap duo, The Coup, are proof that revolutionary rap doesn't have to be boring. This tale of petty hustles leads up to a party where our narrator, Boots Riley, encounters the true hustlers of the world: politicians and corporate fat cats. It's powerful without being preachy. The Coup made waves when the album art for their third album, Party Music, was an image of Boots blowing up the World Trade Center. Its release date? Late September 2001. The album art was finished in June of the same year.

35. Casual "I Didn't Mean To"

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Even Bay Area backpackers were not immune to the East Bay's pimp mentality. Over a jazz saxophone solo, Casual provides a half-assed apology for banging your girl. English students: pay attention to Casual's effective use of the passive voice on the hook.

34. Lil B the Based God "Pretty Bitch"

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Internet phenomenon Lil B the Based God is rarely placed in the larger Bay Area context, perhaps because he collaborates and emulates other Internet-popular acts. But his self-published, self-distributed business model is a sort of update of the '90s model, just without the cassette tapes and the Cutlass to sell them out of. In "Pretty Bitch," B turns Bay Area rap misogyny on its head, sort of. B free associates about how many, and what sorts of, bitches are on his dick. But&#8212and here's where he gets you—he's the pretty bitch, not the girls.

33. Too $hort "I'm A Player"

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A deep, funky bassline, and Too $hort waxing philosophical about being a player. This song is somewhat despair-inducing, as fun as it is. You listen to Too $hort make a compelling case for leaving the square life behind, then you remember that you aren't Todd Shaw, and therefore, are a lame. But it sounds so good!

32. Digital Underground "Freaks Of The Industry"

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"Freaks of the Industry" is an apt moniker for Shock G and Money B, from Oakland's Digital Underground. They weren't quite joke rap; they weren't quite sex rap; and they definitely weren't backpack rap. They were something different. And they were definitely freaks, judging from this song. The song's most famous lines come from Shock G's verse, and provide a sort of sex multiple choice test where it turns out that you're never right. In true Digital Underground fashion, this song about fucking ends with a piano solo.

31. Young Lay f/ Ray Luv and Mac Mall "All About My $Fetti"

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Young Lay is one of the lesser-known rappers from the Crestside of Vallejo, but this song, featuring Crestside resident Mac Mall and Santa Rosa native Ray Luv, was a certified hit. Khayree's unique brand of NorCal G-Funk provides a perfect backdrop to a relatively feel-good track dedicated to the almighty dollar. Young Lay's life would not go as well as this song suggests; he was shot in the head during a botched robbery in '95, and it's a miracle he can still rap today. As the saying goes, more fetti, more problems.

30. RBL Posse "Don't Give Me No Bammer"

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Bammer means bad. Northern California doesn't do bad weed, and Hunters Point duo RBL Posse&#8212Black C and, confusingly, Mr. C—want to make that clear. This song's hook was originally "don't give me no bammer joint, we don't smoke that shit in Hunters Point," but Black C and Mr. C made it city-wide, and created a classic, which virtually everyone who grew up in San Francisco and ever smoked weed is familiar with. Ironically, people from San Francisco aren't against smoking "nade," which makes bad weed "good" by dusting it with bug spray.

29. Mistah FAB f/ E-40, Turf Talk "Super Sic Wit It"

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Mistah FAB is actually a backpack rapper. He put down the backpack when he recognized hyphy's potential, joined Mac Dre's Thizz Ent, and eventually became one of the Bay's biggest stars. If it ever seems like Mistah FAB is just stringing together a bunch of hyphy-sounding things he's heard other people say, it's probably because he was doing just that. That, of course, wouldn't stop him from making this banger, along with many others. Here, he teams up with Sic-Wid-It's hottest prospect, Turf Talk, and its godfather, E-40, over a schizophrenic Droop-E beat.

28. Messy Marv "Get On My Hype"

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Few Bay Area artists have seen more ups and down than San Francisco's Messy Marv, AKA the Boy Boy Young Mess. Since a brief stint in jail, Messy Marv has shed his Bay Area affiliations for The Bloods, and a mountain of cocaine. But, in 2005, Mess was down with hyphy music, even if he wouldn't admit it now. Between his nihilistic growlings, and Droop-E's almost-perfect hyphy track, this song serves as another reminder of how much fun the music was in this particular era. Also, a reminder of just how many different kinds of ecstasy there were.

27. The Pack "Vans"

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Out of nowhere, with a sound like nothing else going at the time, these skate rats from Berkeley made serious waves with this ode to Vans slip-ons, earning them a co-sign and a record deal from Oakland legend Too $hort. Now every other rapper looks like a skater, but this song came out when Dem Franchize Boyz and Mike Jones dominated the airwaves. Of course, because Bay Area rappers are cursed to wither in obscurity, MTV massacred the hook, so that they didn't offer any free advertisement to Vans.

26. Mac Dre "Feelin' Myself"

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In July 2004, Mac Dre released two albums on the same day, Genie of the Lamp and Ronald Dregan: Dreganomics. A few months later, he would be killed while on tour in Missouri. This track, along with "Get Stupid" really were the high point for Mac Dre's ecstasy-influenced hyphy sound. When Dre says he's feeling himself, he means he's on a shitload of ecstasy. In the '90s, when that drug was associated with glowsticks and JNCOs, who could have imagined that one man, Mac Dre, would introduce the drug to the world of sideshows, fifths of Hennessy, and Backwoods blunts?

25. Cellski "Livin in the Bay"

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On this banger, off his classic debut, Mr. Predicter, Cellski shows off his chops both as MC and producer. Over a sampled Spice 1 line, an eerie X-Files-esque whistle, and a chunky bassline, Cellski makes a case for how hard "San Franpsycho" can be, despite what you've heard. While quite popular locally, Cellski never got much recognition outside of the Bay Area, except for a one-second cameo is Lil Flip's video for "Sunshine," and, strangely, when he witnessed an air terror scare shortly after with the "Underwear Bomber," and his twitpics were circulated by all sorts of media organizations.

24. Spice 1 "Trigga Got No Heart"

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While not as famous as another song on the soundtrack, MC Eiht's "Streiht Up Menace," Spice 1's "Trigga's Got No Heart" does just as good a job encapsulating the defiant and reckless feel of Menace II Society. In classic early '90s fashion, the East Bay Gangsta gets his fake Patois on for the cold-blooded hook. This song would later be reprised as "Killa Kali," the lead single off of Yukmouth and C-Bo's Thug Lordz album.

23. TWDY f/ Too Short "Player's Holiday"

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Oakland producer Ant Banks put together a sort of Bay Area supergroup called T.W.D.Y. (The Whole Damn Yay) with Rappin 4-Tay and Captain Save-Em. This song, released at the end of last century, is a great document for those studying Clinton-era optimism; the premise of the song is that the president has gotten rid of all the player haters, and there is now a holiday commemorating the day. The video takes place on a yacht.

22. Mac Dre f/ Mac Mall & Miami the Most "Stupid Doo Doo Dumb"

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Peppered with manic adlibs from Dre's erstwhile, aging sidekick Miami the Most—who claimed he was dropped in glitter as an infant—"Stupid Doo Doo Dumb" is exemplary of the kind of music Mac Dre was putting out after being released from jail on pizza parlor robbery charges, but before he started doing lots of ecstasy. It's still gangsta-rap influenced, but it's starting to get goofy. Also, this would be, I think, the last time Mac Dre and Mac Mall would appear together on a song until their beef-squashing reunion album Da U.S. Open with Andre Macassi and Mall Macenroe.

21. The Jacka "Barney (More Crime)"

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In the middle of the last decade, a new sound started to come out of the small, quasi-suburban city of Pittsburg, in the Northeast Bay Area. Jacka and Husalah, members of the Mob Figaz, were putting out gangsta rap with a conscious aftertaste, often including moody, sing-songy hooks. "Barney (More Crime)" is arguably the best example of this sound; it retains a certain Bay Area silliness&#8212calling purple weed Barney, for instance&#8212but still manages to be a deeply emotional song. That is no easy task.</p>

20. Celly Cel "It's Goin Down"

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Vocoder, deep bubbly bass, and an 808: you can practically see the palm trees vibrating in the rear view's reflection, Celly Cel's jheri curl dripping on the leather of his headrest. Some songs are tough to explain because they're just perfect.

19. Del "Mistadobalina"

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Ice Cube's cousin, Del the Funkee Homosapien, clearly inherited his family's talent on the mic, but also took things in a different direction, favoring laid-back lyricism over the righteous anger that characterized so much of Cube's catalog at that time. On this track, Del kicks three verses handily clowning on some square named Bob Dobalina, over a jazzy breakbeat. Few songs have more bogus backstories than Del's "Mistadobalina." There never was anyone named Bob Dobalina, he's just a stand-in for the typical second-person sucker that so many rap songs depend on. The name, in fact, comes from a sample of The Monkees' song "Zilch."

18. Lil Bruce "Mobbin in my Old School"

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Little Bruce may be the most slept-on rapper from Vallejo, an "itty bitty city" of about 100,000 that probably leads the nation in slaps per capita. This track, off of his debut album, XXXtra Manish, is an ode to another Bay Area rap tradition: doing stupid shit with cars. While Jay-Z would reserve this Isaac Hayes sample for his thoughtful "Can I Live?," a couple years earlier Studio Ton and Little Bruce made an infectious hook about 23109 violations (CA police code for exhibition of speed, also the title of a popular sideshow DVD) .

17. JT The Bigga Figga "Game Recognize Game"

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JT the Bigga Figga, from San Francisco's Fillmore District, embodies both the best and worst of the independent entrepreneurial nature of Bay Area rap music. He released all of his own music, even a book on how to become a successful black CEO&#8212called Black Wall Street, that would somehow become The Game's ill-fated label&#8212but little other than &#34;Game Recognize Game&#34; is all that memorable today. Of course it&#39;s the lesson of the song that you have to respect what JT did, so in that spirit, Get Low to this one next time you hear it.</p>

16. Mac Mall "Let's Get A Telly"

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One of many Macs from northern Vallejo, Mall was far more popular in the '90s than Dre ever was, and managed to avoid beef with 40's Sic-Wid-It Records, from the south side of Vallejo (though he didn't manage to avoid having a brief beef with Mac Dre himself). While his first record, Illegal Business?, is an undeniable classic, this track off of his sophomore effort, Untouchable, was a bigger hit for being, well, better. Khayree produced this track, and much of the biggest non-E-40 hits out of Vallejo in the early '90s. Over Khayree's keyboard and blown-out synths, Mall picks up freaks from a house party. It also includes the unfortunate phrase "hands on her cock."

15. Andre Nickatina f/ San Quinn "Ayo"

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Andre Nickatina (nee Dre Dog) teams up with fellow Fillmore MC San Quinn for this ode to the perils of cocaine abuse. Nickatina quit the powder some time in the '90s, toning down his cocaine-rage sound to a more marijuana-influenced one. Ironically, this song is incredibly popular with sorority chicks and fraternity bros who do cocaine.

14. E-40 f/ Suga T "Sprinkle Me"

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40 and his sister go back and forth over a lighthearted Sam Bostic beat, providing a bit of levity to 40's only perfect album: In a Major Way. This album is so perfect, in fact, that despite its popularity, "Sprinkle Me" might be one of the weaker tracks on it. That said, E-40 laces the listener with plenty of game on this one, including a new place to hide a 40—your ballcap.

13. Too $hort "Freaky Tales"

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Before Todd Shaw made a name for himself by cussing, he did so by telling his "Freaky Tales." He would later reprise this with "Freaky Tales 2," "More Freaky Tales," and, of course, "Cocktales." Never once does Too $hort explain what "TP treatment" is, but if you think really hard about it, you can probably figure it out.

12. 2Pac f/ Digital Underground "I Get Around"

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2Pac, before he was 2Pac, was a dancer for Digital Underground. Here, he teams back up with his old road dogs, and tones down the self-seriousness that characterized so much of his catalog, instead chasing tail, and partying poolside. On this ode to "No Strings Attached" sex, Tupac even manages to reference WWII-era propaganda—"loose lips sink ships." Pac and the Underground go a little easier on the ladies than, say, Too $hort might have, but the Bay Area player mentality is strong here. Also, we learned that Money B drinks Michelob.

11. The Federation "Hyphy/Hyphy Remix"

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The Federation "Hyphy"


While "Super Hyphy" might be the track that launched Hyphy music on to a larger-than-regional stage, The Federation—from Fairfield, which is just barely part of the Bay Area—kicked things off a few years earlier over this scat-inflected Rick Rock beat. The beat, in fact, was supposed to go to Mistah FAB, leading to a minor intra-Bay beef between Fabby and the Federation that no one ever really cared about. The remix to the song with Turf Talk, San Quinn, and Keak da Sneak got countless spins on Bay Area radio, ushering in a new era where local artists actually got airtime on KMEL and KYLD. This, like the FAB/Fed beef, would be short-lived.

10. Dru Down "Pimp of the Year"

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The Bay Area was home to Fillmore Slim, and the setting for 1973's The Mack, and you better believe no local rapper is going to let you forget either fact. This occasionally creepy song was an unlikely hit in the Bay Area in the '90s, toned down to "Mack of the Year," with much of the violence against women removed. Dru Down is one of those people who you can tell, from his voice, that he has a jheri curl.

9. Digital Underground "Humpty Dance"

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MC Humpty, one of Shock G's many alter-egos, wears Groucho Marx glasses and has his own inscrutable dance that is most likely just fucking. Humpty's buffoonish pimp persona, when placed in Bay Area context, is hard not to read as some form of parody of his contemporaries in Oakland. In any case, the song managed to make lumpy oatmeal and Burger King bathrooms seem somehow obscene.

8. Dre Dog "Smoke Dope and Rap"

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Dre Dog's ode to marijuana and cocaine—when put together, in local parlance, "chewy"—is still perfect eighteen years later. The lazy, eerie bassline sample, from The Southside Movement's "I've Been Watching You," encapsulates perfectly the disorienting combination of uppers and downers. This song is so full of excellent one-liners it's hard to keep track, but keep your ears open, and you'll hear the name of one of the most popular hip-hop blogs going these days.

7. Keak da Sneak "Super Hyphy"

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This is perhaps the only, truly perfect record to come out of the "Hyphy movement," as it was known in 2006. Traxxamillion's smooth, bouncy beat provides a nice contrast to Keak's Newport-addled rasp, and its hardly weighed down by typical Bay Area pettiness about stolen slang. If you can't tell, on the hook, Keak is saying "I don't think they know that's my word," referring to the word "hyphy," which he coined. It's a portmanteau of "hyper" and "fly." Weren't you happier not knowing that?

6. Mac Dre "2 Hard 4 The F-ckin' Radio"

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Mac Dre never scored a hit outside of the Bay Area in his fifteen-year career, despite being a hero to everyone from the cuttiest of Oakland dopeboys to the stoniest of Truckee whiteboys. Aside from the prominent use of fuck-words on the hook, this song is hardly that hard—it actually sounds wholesome next to so many other tracks on this list. It's almost as if the hook were written that way to prove a point. Andre Hicks swore off radio play in the early '90s with this song—though this track would get spins as "2 Hard 4 the Funky Radio"&#8212and wouldn't see much airplay until after his tragic death in 2004. Bay Area radio stations KMEL and, to a lesser extent, KYLD have found themselves in and out of Bay Area rapper's good graces&#8212and vice versa&#8212at several points, depending on how much local music they played. Both Too $hort and Mistah FAB recorded KMEL diss tracks at different points in their careers. Mac Dre came around on KMEL later in his career, recording an ode to Morning Show host Chuy Gomez on <i>Al Boo Boo</i>, &#34;Chuy.&#34;</p>

5. E-40 f/ The Click "Captain Save A Hoe"

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This song is an odd blend of misogyny and excellent family values. E-40, his sister Suga T, his brother D-Shot, and his cousin B-Legit trade rhymes about what a bad idea it is to spend money on women. In Vallejo, it IS trickin' if you got it, and E-40 created an excellent superhero character to mock this sort of behavior. E-40 would later introduce Lieutenant Roast-a-Botch, who was Captain Save-a-hoe's opposite, while a rapper would adopt the radio edit name "Captain Save Em," as part of Ant Banks' short-lived TWDY group.

4. Souls of Mischief "'93 'Til Infinity"

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"93 'til Infinity" is an undeniably dope laid-back track from a crew reppin' a city—Oakland—that gets "a little hectic," as they point out in the intro. Despite haling from a place best known for its aggressive gangsta rap and high crime rate, The Hieroglyphics crew provided a nice contrast to all the chaos, cusswords, and sideshows. Making the biggest national impact from Hiero was the four man crew of A-Plus, Opio, Phesto, and Tajai, collectively known as The Souls Of Mischief. Their emphasis on innovative rhyme schemes, and having fun, resonated from coast to coast and was on full display here. Their lyrics were witty, funny, and playful, while their chemistry and ease passing the microphone in mid-verse proved to be irresistible and sounded amazing.

3. Rappin' 4-Tay "Playaz Club"

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Arguably San Francisco's only real nationwide hit, "Playaz Club" is an ode to speakeasys that most likely never existed. 4-Tay imagines a world of dominoes, mink rugs, body rubs, and endless champagne. 3rd and Newcomb, shouted out at the end of the song as the location of Hunters Point's Player's Club, is home to Bayview Liquors. While Bayview Liquors is not a speakeasy, you can still buy San Francisco specialty cocktails there, like Cutty Bangs and What-it-dos: bags of mini-bottles of booze, with special mixers and a red cup. It's a party in a bag.

2. Too $hort "Cusswords"

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While East Coast rappers were scared to use cusswords on wax, Too $hort was in Oakland stringing together as many as he could—"motherfuck you damn shithead bitch"&#8212eventually taking credit for making the word "bitch" or "beeyatch" as popular as it is today—which, whatever. This is also probably the first instance of a rapper claiming to have received fellatio from the First Lady, while accusing the president of dealing cocaine. Despite being ahead of his time with regard to cussing, $hort still had an old school attitude towards song length. Having the most raps, or being able to rap the longest, was still considered a worthwhile endeavor. At seven minutes forty-five seconds, with no throwaway lines, "Cusswords" is a whale of a song by today's standards.

1. Luniz "I Got 5 on It/I Got 5 on it Remix"

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Luniz - "I Got 5 On It"


Few beats are so inextricably linked to a specific drug in the way that this song's sample of Club Nouveau's "Why You Treat Me So Bad" makes you think immediately of weed—something that made it an odd choice in more recent years, when Diddy sampled it for a heartfelt R&B collabo with R. Kelly, "Satisfy You." A remix featuring every rapper from the Bay Area who mattered at the time—Richie Rich, E-40, Dru Down, Spice 1, and Shock G, but not Too $hort, for he and Yukmouth had a long-standing beef—would be even more popular than the original in The Bay. This is a shame, because Yukmouth and Numskull really get in-depth on the topic of weed smoking etiquette on this track, with the mellifluous Mike Marshall hook as the icing on the cake—there's a lesson in here for everyone. This song was also wildly popular outside of the Bay Area, which is atypical of most Bay rappers' stories (you may have noticed this). Not only did Numskull and Yukmouth bump Michael Jackson from the top of the U.S. charts with this ode to going Dutch on a ten-sack, they also topped the charts in many European countries.


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