Top 10 Defining Moments in Too $hort's Legendary Career

Fans have come to appreciate Too $hort as more than the narrator of inappropriate freaky tales but also as a calculating businessman and hugely successful rapper. Here are the standout moments from his career.

Too $hort is a hip-hop legend, a foundational West Coast artist, a titan of Bay Area rap, and — more than anything else — a survivor. This funny and funky rapper chronicled the street life of Oakland and beyond beginning in the cassette era, and will soon stream an album with supergroup Mt. Westmore alongside heavyweight peers Snoop Dogg, Ice Cube, and fellow Bay Area stalwart E-40. $hort has remained relevant for decades by subtly switching up his sound to reflect the times, while mostly rapping about a few distinct subjects, and making hits with a variety of collaborators. Listening to Too $hort rap is educational. Though primarily known for his Blaxploitation-inspired observations of the streets over slow rolling bass lines, a close listening of his catalog reveals several more layers. 

There are cautionary tales, incisive social commentary, constant assertions of community pride, and party songs. $hort’s trademark high-pitched voice and plainspoken delivery makes his music accessible to people worldwide. However, the defining quality of his music is the glorious and constant profanity that recalls classic comedy records and elaborate pimp chatter. As youngsters growing up in the Bay Area, we had to sneak away to listen to Too $hort tapes, stealing access to the colorful world of characters he describes — the triumphs, the failures, the celebrations, the dangers of a heightened urban landscape. 

As the years progressed we have come to appreciate Too $hort as more than the narrator of inappropriate freaky tales but also as a calculating businessman and hugely successful rapper. The way he survived the streets, critical backlash, and dozens of stylistic shifts in trends to still be near the top of the game is one of hip-hop’s great stories, and we deeply admire his resilience and commitment to his core aesthetic. 

Here we break down some of the key moments in $hort Dog’s astounding run in celebration of a hustler who made it, setting an example for strivers in diverse artforms worldwide. 

One more note: we were blessed to be able to speak to the man, the myth, the legend for the 200th episode of our hip-hop discussion podcast Dad Bod Rap Pod. $hort was magnanimous and funny, with a surprisingly sharp recall of his entire career, from the streets to the studio. Our tribute podcast episode will be streaming everywhere on December 23, 2021 via the Stony Island Audio podcast network.

1. Begins Recording Personalized Tapes

The story of Bay Area rap is about entrepreneurship as much as it is about music. From E-40 slangin' music in his hometown of Vallejo to Master P founding No Limit Records out of a small storefront in Richmond to indie MCs in the Living Legends collective selling tapes out of backpacks on Telegraph Avenue in Berkeley, Bay Area artists have never waited for validation from major labels to build a fan base. The “out the trunk” ethos of selling music directly to fans was pioneered, in part, by a young Too $hort in Oakland in the early '80s. A prolific rhyme writer and tape creator already, $hort struck street gold when he realized that the local players would pay a premium for a custom shout-out on one of his tracks. As $hort described it on Netflix’s Hip-Hop Evolution, “Everybody who was the boss of anywhere, who felt like he was important, would give us $20 for a custom-made tape. And the shit just took [off] from there.”

This legendary hustle acts simultaneously as an origin story for the prolific and wildly successful rapper, as well as an indication of how much of hip-hop culture has always been intertwined with the streets. Many of the best rappers are observant and artistic, great writers who are in the streets enough to understand how they work and then turn the actions they witness into narratives for listeners to take in at a safer remove. —Nate LeBlanc

2. The 75 Girls Era 

At 8 minutes — and 10 verses! — “Cocaine” is an anti-drug warning that abhors addiction and the havoc it wreaks; told through the perspectives of different drug addicts, but mainly that of a female protagonist. On it, $hort laments, rather uncharacteristically: “Right now today, in '85, you better stop smoking, while you're still alive.”

Just a few years earlier, on 1983’s Don’t Stop Rappin’, he was referring to himself as “Sir Too Short” and directed malice towards “Sucker MCs.” By ‘85, however, gone were mentions of “Sir”— we’re introduced to “Playboy Short” weirdly juxtaposed with an intense “Say No To Coke” single. Yet that sense of unpredictability and mixed messaging underscores this early era, one where Short’s pimp persona was being developed, and where his relationship with the label’s founder, Dean Hall, was just at its start. West Coast rap, even Too Short’s, was still shedding remnants of East Coast styles it parroted from the early ‘80s. 

Hall and 75 Girls would go on to release $hort’s earliest material, homespun tracks of increasingly salacious rhymes over minimal, keyboard beats. These projects set world records for use of the word “bitch,” yielding unforgettable classics like “Blowjob Betty” while adding Oakland to the list of new rap regions.  —David Ma

3. Too Short “Can’t Rap” Discourse 

Since the dawn of hip-hop, there has been an ongoing debate among rap fans and practitioners about who can and cannot rap. This may seem like a silly debate to modern rap listeners — as the definition of what good rapping is has broadened to include more regional, melodic, and just different styles beyond hardcore lyricism. But in the halcyon days of the late '80s and early ’90s there were definitely hard and fast rules about what constituted good rapping, a kind of gatekeeping enforced by East Coast hip-hop magazine editorial offices. Too $hort and his west coast player narratives definitely did not fit within that rubric.  

His slow and deliberate cadences were dripping with Oaklandish authenticity, but he was not considered witty or lyrically dexterous enough for the East Coast rap intelligentsia. Too $hort was well aware of the perception that he couldn’t rap and yet he pressed on, completely undeterred. During his guest verse on E-40’s 1996 song “Rappers’ Ball” $hort Dog jabbed back at his critics with his patented nonchalance ‘They sad I couldn’t rap I only say “Bitch / I guess the bitch made me rich.”  —Demone Carter

4. Get in Where You Fit In Is Released 

Too $hort albums in the Jive Records era arrived at a steady clip, every year or two, and kicked off with spoken intros that are essentially an accounting of his phenomenal success as a recording artist up to that point. The first line off of Get In Where You Fit In's intro  “Don’t Fight The Intro” also acts as sage life advice: “Get mad if you want, I won’t front, ‘cause I got a new tape and it’s full of bump.” Get In Where You Fit In is one of $hort’s major works.

The album details Short’s everyday existence in East Oakland, in particular the local travelogue “Just another Day” and the recounting of a relatively brief dry spell in “Gotta Get Some Lovin'.” Short also breaks down neighborhood socioeconomics over a recognizable sample on “Money In The Ghetto." However, the reason to keep returning again and again to this record is the loping bass line and autobiographical lyrics of “I’m a Player,” the kind of song that is played to this day in custom cars, strip clubs, and earbuds, encapsulating what makes Too $hort a great artist; the fact that he made it makes the listener feel that they can make it as well. — NL

5. “Gettin' It” Becomes a National Hit 

With Gettin' It (Album Number Ten), $hort was already teasing the notion of retirement, calling it the “last album.” He’d been in the game for about 13 years and scored a big national hit with “Gettin’ It.” Its music video was not for the envious; scenes of fiery suitcases presumably filled with explosive riches, as well as ennobled cameos from Ice-T and Coolio (whose “Gangsta’s Paradise” was a gargantuan, ubiquitous hit prior to becoming a cultural punchline). Parliament Funkadelic too was in the video, in full regalia, dancing on stage, a fear-of-missing-out moment if there ever was one. Here, Short reminds us of his ascent: “You see I got all my game from the streets of California. Young millionaire with no high school diploma.” 

Gettin’ It went platinum, making it Short’s fifth at this point. He eventually took a three-year hiatus, the longest break in between albums since the early run with 75 Girls. In a year and landscape of new sounds that included De La Soul's Stakes Is High and ATliens, Gettin’ It stood out by offering the familiar — pimp tales and g-funk, becoming another triumph for the Oakland Mack. —DM

6. The Move to Atlanta 

The do-it-yourself ethos that fomented out of Too $hort’s trunk bubbled up and spread across the country. The aforementioned rap mogul Master P cut his teeth in Richmond, CA before taking his No Limit empire back to New Orleans. Bay Area rap impresario E-40 leveraged southern markets to build the independent juggernaut Sick-Wit-It Records. Too $hort has also played the role of Bay Area rap ambassador of sorts. In 1993, $hort Dog moved from Oakland to Atlanta to escape rising tides of violence and embrace the party lifestyle best personified by the Freaknik festivals. $hort’s arrival coincided with the formation of an emergent Atlanta music scene led by music mogul L.A. Reid and producer Dallas Austin. The “player” sound and aesthetics that Too $hort brought to rap music are prevalent on Outkast’s debut record Southernplayalisticadillacmuzik, an album that helped catapult the dirty south out of regional rap obscurity. 

While Too $hort is careful not to give himself too much praise for the role he played in the emergence of the Atlanta music scene there is no doubt that transplants like himself and Erik Sermon were important co-signs as A-Town sought to break free from the East Coast, West Coast binary. Too $hort also formed a relationship with a So So Def records A&R and local DJ by the name of Lil Jon. The friendship would eventually bear fruit with Lil Jon producing hits for $hort.  — DC

7. Too Short and Dave Chappelle "Bitch!" Synchronicity 

Not surprisingly, Too $hort's influence extends beyond rap music. For good or ill his usage of the word "Bitch" — and the unique Oakland-inflected pronunciation of it — has held a place in the zeitgeist for some time. Case in point, comedian Dave Chapelle co-opted it as part of his catchphrase “I’m Rich Bitch.” The phrase was clearly an homage to Too $hort, one that $hort referenced noted on his 2006 hit “Blow The Whistle” when he rapped “...he got it from me and made $50 million dollars, I’m proud of you G.” 

$hort seems both genuinely flattered by the use of his trademark slang and also wanted to make sure proper credit was given. But the similarities between $hort Dog and Chapelle don’t stop there; both artists have managed to thrive even as the cultural climate has shifted away from the misogyny that both artists have gleefully reveled in. — DC

8. His appearance on American Pimp

A clip of Too $hort’s song 1990 song “Pimpology” from the Short Dog’s In The House album, as well as an on-camera interview where $hort details the connections between rapping and pimping  is a pivotal moment in The Hughes Brothers’ 1999 documentary American Pimp. The film leaves the brash personalities and flowery language of its old-school characters aside at this point, and begins to focus on a colder, more callous breed of pimp, those of the hip-hop generation. Here the filmmakers begin to focus on the darker side of street life, the consequences of the reprehensible actions of the people profiled in the documentary. 

However, they have $hort hop into the film for an interview in the bright sunlight to run down the tenets of the game. “Pimpology” lays out the rules of the sex racket the same way that Notorious B.I.G’s “10 Crack Commandments” would for drug dealing a few years later. In both cases a savvy wordsmith draws the curtain back on a cloistered culture, allowing the listener access to otherwise foreboding existence. Hip-hop and the language and culture of pimping have always been closely aligned, and this moment in the film illustrates the connection, bringing new ears to an album cut from one of $hort’s earliest smash albums. - NL

9. "Blow The Whistle" Blows

Generations of listeners have different entry points to $hort’s body of work. After all, hits like “Life Is… Too Short” was a decade removed from “You Nasty." $hort’s been steadfast in his devotion to a foundational sound, but with an acute ability for relevance through changing times.

The common refrain is that "rap is a young man’s game" but by 2006, Short had been in the business for over a decade and was already 40 years old. And “Blow the Whistle” has become one of his defining songs.

By early 2005, Hyphy was enveloping Northern California and “Blow The Whistle” stands as one of the most memorable cuts from that era. Recorded in 2006, it was produced by Lil Jon on Short’s album of the same name. It was an attempt by Lil Jon and stalwarts like E-40 to advance Hyphy from a localized movement to the national stage. Jon has been quoted as being somewhat unsure of “Blow The Whistle,” not entirely confident it would catapult Hyphy as they wished it would’ve. While the Hyphy movement came and went, it’s clear that “Blow The Whistle” has made cultural inroads, evidenced by its repeated use in Hollywood through the years — as recently as this year on the HBO show Insecure. — DM

10. The Mt Westmore Era

In a 2019 interview with Vibe Magazine, the great E-40 had this to say about Too Short: “I used to go to every Too Short show I could. I don’t look up to too many, but I looked up to him. I grew up on all his stuff… the grind didn’t stop from there though, we went on to do hella songs.”

“Rappers’ Ball” was their first big collab, a moment of envy for all rappers which appeared on E-40’s Tha Hall of Game.  The video shows West Coast elites partying with Ice-T and Tupac while luxuriating in their successes. Both E-40 and Short were at one point on Jive and would elevate their partnership as the decades went on, an easy alchemy that produced work like History: Mob Music and History: Function Music, amongst others. 

It’s fitting then that the supergroup Mt. Westmore would be Short and 40 with two other icons of the same ilk, Snoop Dogg and Ice Cube. According to Short, they have 50 songs recorded. The level of productivity is no surprise but the talent level is brimming. It also marks a career stage that is the culmination of decades of work, perseverance, and influence. Even at a juncture of elder statement status, Short has an innate agelessness to him, bereft of any signs of slowing, while careers around him dovetail. At 55, he’s a legend that walks amongst legends. We very much look forward to decade number 6 and beyond. - DM

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