I. “Eight years on the mic and I'm not joking, Sir Too $hort comin' straight from Oakland…”
“I must have superpowers, rap for 225 thousand hours,” Too $hort proclaims on “Blow The Whistle,” the title track off his sixteenth solo album and, arguably, his best-known hit. Coming from this true living legend and spinner of fictional freaky tales, this enormous calculation has a remarkable ring of truth. Across a now four-decade-long career, Too $hort has released twenty-one solo albums, three collaborative works (with E-40 and Mount Westmore, respectively) as well as numerous compilations, EPs and mixtapes. His emergence in the 1980s helped establish Oakland as a hub of early rap activity rivaling L.A., emboldening the West’s footprint in hip-hop.
Selling tapes hand-to-hand at a time when the East Coast still had a vice grip on rap audiences, Too $hort—born Todd Shaw—made homespun songs that reverberated instantly with local audiences, but would come to be revered worldwide. Rap was still trickling to areas outside of New York’s mecca, at a time when marquee acts like Whodini, Kurtis Blow, and Run DMC were all gaining commercial traction. For $hort, however, rhyming was a natural extension of his affinity for drums.
In a 2021 interview with Dad Bod Rap Pod, a weekly podcast which I co-host, he explained how his interest in percussion intersected with rap’s commercial rise. “I was a drummer in a school band, since probably like sixth or seventh grade,” $hort said. “I was getting really good at reading music and I knew how to play. Hip-hop records came out in 1979 and I first heard ‘Rappers’ Delight’ in the ninth grade. It was the first commercial hip-hop record that got big. After that, I started buying anything that was hip-hop: Grandmaster Flash, Spoonie Gee, and a few other records in those early days.”
In the summer of 1980, the Los Angeles-born $hort relocated with his family to East Oakland. There, he attended Fremont High School, deepening his roots in the city and community where he would become a mainstay. “This was early on and I only heard rap like a year or so earlier,” he said. “So, as a drummer who’s always thinking of patterns, I was like, ‘I can do this shit.’”
His first song attempts utilized whatever was at his disposal, often random jazz or funk records. As he explained in our 2021 interview: “I remember I found a jazz record with like four songs on it and it was all instrumental. But one of them was really funky. So I sat a tape recorder next to the speaker and just rapped along to the instrumental, so it would all record at once. That was just me checking the temperature to see if I could flow. Then, it was mostly Parliament [Funkadelic] that I was into—I was obsessed with the funk. Even in my pursuit to find things to rap over, it still always had to have that funk. As time went on, I just wrote more lyrics and got better and better.”
As these tapes started to gain popularity in his neighborhood, $hort dubbed his own cassette copies and spread them all over East Oakland. “By 1981, I was like, ‘I’m a rapper,’” he said.
II. “This one-of-a-kind rapping style, had the freaks in the back just going wild…”
The saga of Bay Area rap is a tale of the convergence of creativity and entrepreneurship. Giants like E-40 in Vallejo and Master P in Richmond could be found in the ’90s perched on busy downtown strips selling music directly to fans. In this pre-internet era, this was the very definition of being an independent artist: Eschewing the music industry, cutting out middlemen, and reinvesting back into yourself and your art. $hort was the paragon of this hustle, with an unprecedented approach of including real-life neighborhood characters—the pimps, the hustlers, the OGs—into the songs themselves.
The idea of making custom songs was something he came up with alongside his high school friend Freddy B, a lifelong business partner and artist who was instrumental in $hort’s early ascent. As $hort explained on Netflix’s Hip-Hop Evolution: “Everybody who was the boss of anywhere, who felt like he was important, would give us twenty dollars for a custom-made tape. And the shit just took off from there.” What soon developed would be different eras of music that encompassed Todd Shaw the person, Too $hort the rapper, and composite characters like $horty The Pimp or Playboy $hort—local celebrity hustler types whose stories aligned with the streets. “1982 was the height of me and Freddy B selling tapes all over the city,” $hort recalled.
Forging his independent ethos even further, he upgraded his entire business plan a year later, using professional studio space and equipment to proliferate music on an even greater scale. In 1983, $hort signed to 75 Girls, an independent Oakland label founded by Dean Hall. His official debut album was that year’s Don’t Stop Rappin’, where he started referring to himself as “Sir Too $hort” and, as many in that era did, directed malice towards “sucker MCs.”
$hort explained this evolution thusly: “It was a big deal to own a drum machine back in those days. And Dean had all that shit—all the best drum machines, all the best equipment, all the best instruments. It was the best of the best and I stepped into this shit with a lot of material; pages and pages of rhymes.”
By 1985, gone were mentions of “Sir Too $hort”—we’re introduced at this time to “Playboy $hort,” a pimp character with overt complexities and contrasts, as heard on the intense single, “Cocaine.” At eight minutes long, “Cocaine” is an anti-drug warning that abhors addiction and the havoc it wreaks, told through the perspectives of different 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.”
This sense of unpredictability and duality underscores $hort’s early developmental phase, one where his pimp persona was still being workshopped. West Coast rap, even $hort’s, was still shedding remnants of East Coast styles it parroted from the early ‘80s.
III. “I got more respect than you'll ever get, ‘cause I don't stop rapping and you know that shit…”“
As he developed a national profile, endearing himself to new audiences while keeping up with ever-growing demand for his music, $hort found he was sitting on evergreen material in the form of those early mixtapes, which had been little heard outside of the Bay Area. “In those early tapes, I recited lyrics I would later use for probably my first eight albums on Jive,” $hort explained to me with a laugh. “I was repurposing a lot of lyrics from those Freddy B tapes we did. If I wrote it down on paper and it was in my shoebox or something, one day, years later, I’d come back and rewrite all that shit. For example, “Freaky Tales” I wrote in 1982 but the version everyone knows is the one I rerecorded in 1987.”
That version would appear on Born To Mack, originally released through Dangerous Music, a label he co-founded with Freddy B in 1987. $hort’s fourth studio album, it was picked up by RCA and released on CD by Jive a year later, marking his first major label effort and the start of a fortuitous, decades-long relationship with the British-American label. Lore has it that $hort sold fifty thousand copies of Born To Mack out of the trunk of his car alone. A moment of triumph, it was a time when $hort’s long game coalesced. These Jive years produced some of his most revered material.
Life Is… Too Short was the next big one. Similar to Born To Mack, it was originally released by Dangerous Music in 1988 and re-released a year later by Jive, becoming perhaps $hort’s most renowned full-length. In a moment of manifesto-like introspection, the album’s classic title track offered the following wisdom: “You can take back all the things you give, but you can't take back the days you live. Life is to some people heaven on earth, living every single day for what it's worth. I live my life just how I please, satisfying one person I know, that's me.” At this juncture, still just under a decade into this rap vocation, $hort was reaping the rewards of what had started only eight years prior. Decades later, Rolling Stone would cite Life Is… Too Short on their list of the 200 Greatest Hip-Hop Albums Of All Time.
$hort’s run at Jive would continue apace through the ’90s. In a piece for Okayplayer, writer (and Dad Bod Rap Pod co-host) Nate LeBlanc neatly summed up another of $hort’s stellar works, 1993’s Get In Where You Fit In: “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.”
Around 1993, $hort moved across the country to Atlanta and quietly embedded himself into the city’s burgeoning music scene. Short Dog’s In The House and Shorty The Pimp followed, adding to an already epic mid-’90s run.
With his tenth album, 1996’s aptly-titled, Gettin' It (Album Number Ten), $hort was already teasing the notion of retirement, calling it his “last album.” He’d been in the game for over a decade, and scored a national hit with the lead single “Gettin’ It.” Its music video was not for the envious, with scenes of fiery suitcases presumably filled with explosive riches, as well as ennobled cameos from Ice-T and Coolio, then riding high on the back of“Gangsta’s Paradise”
$hort also made sure to include his favorite group, Parliament-Funkadelic, in the clip, with members of funk’s high kings dancing on stage in full regalia. On the song, Short reminds us of his quick yet explosive, self-made ascent: “You see I got all my game from the streets of California. Young millionaire with no high-school diploma.”
In a year where the rap landscape was changing rapidly, typified by albums from established groups offering fresh new sounds like De La Soul's Stakes Is High and Outkast’s ATLiens, Gettin’ It stood out by offering the familiar—pimp tales and G-funk, yet another notch in the belt for the Oakland Mack.
Gettin’ It went platinum and $hort did retire, at least temporarily, enjoying a three-year hiatus—his longest break between albums since the 75 Girls era—before returning in 1999 with the aptly-titled Can’t Stay Away.
IV. “So keep your jealous-ass thoughts in your diary, and if you're looking for a leader, you can hire me…”
For Too $hort, the decades of classic music is all the product of a simple formula. “For me, there’s three layers to a song or album, three things that always had to happen throughout,” $hort says, reflecting on his musical approach through the years. “It has to be funny as fuck, pimp and player as could be, and balance all that with real fucking issues that are really happening today. I grew up listening to Redd Fox and Richard Pryor…and humor was always very important to me. It was a deliberate shock value that had always worked forever for me since we were doing street tapes.”
As the ’90s came to a close, $hort found himself in a rare position in hip-hop: A living legend, still cranking out commercially viable new music. Moving into the new millennium, his recording career was back in full swing: He averaged about an album a year, with You Nasty (2000), Chase The Cat (2001), What’s My Favorite Word (2002) and Married To The Game (2004) all dropping through Jive.
$hort’s next release intersected with the rise of Oakland’s hyphy movement, a genre of aggressive, hyperactive songs that soundtracked Bay Area sideshows, informal and illegal gatherings of car stunts held in public spaces. Broadcast wide through DVD mixtapes and early forms of social media, the antics and music started earning nationwide attention. Stalwarts of the movement like Mac Dre, Messy Marv, Mistah F.A.B., Traxamillion, and Keak Da Sneak all contributed to this hyper-local scene that began to explode across the country.
2006 was a pivotal year for hyphy, as E-40’s “Tell Me When To Go” blanketed radio and TV. Internally, however, the local scene was fizzling out just as it hit the mainstream consciousness. “Blow The Whistle,” the lead single of his 2006 album of the same name, undoubtedly reinvigorated and further popularized the movement.
Blow The Whistle was another testament to $hort’s creative longevity, one that introduced him to a whole new generation of listeners, many of whom were likely unaware that he’d been in the game for decades. The common refrain is that rap is a young man’s game but $hort, already forty years old at this point, generated a new level of momentum with this project, matching or perhaps surpassing the buzz generated during his ’80s and ’90s heyday.
The sixteen-track project featured a convergence of Oakland street life and low-end bombast, anchored by rumbling bass and jutting synths tailored for the tastes of aggressive partygoers or sideshow regulars. For the guest list, $hort enlisted iconic heavyweights like Snoop Dogg, and will.i.am, Rick Ross, Pimp C and Tha Dogg Pound, adding a musical diversity to the project.
Yet it was Atlanta firebrand (and the producer of E-40’s aforementioned “Tell Me When To Go”) Lil Jon, who produced six songs on the album, that made the largest splash with his beat for “Blow The Whistle.” The track was a mushroom cloud, becoming fodder for every club DJ thereafter, with remixes galore propelling it even further worldwide. $hort’s always had steadfast devotion to his foundational sound, with the acute ability to update it through changing times; “Blow The Whistle” became a perfect encapsulation of this knack for subtle reinvention.
Despite not initially charting, “Blow The Whistle” quickly became one of $hort’s best-known songs. On it, he hypothetically asks the listener: “What’s my favorite word?” At this juncture of his career, anyone who’s heard his music before already knows what to shout: “Bitch!” It also stands as another victory between $hort and Jive, a most fruitful business relationship if there were ever one.
While hyphy came and went, “Blow The Whistle” made long-lasting cultural inroads, evidenced by its repeated use in Hollywood through the years in films like 2023’s Scream VI or in popular shows such as Insecure or Euphoria. Remakes by Drake and Saweetie added to its sense of permanence. Says $hort, reflecting on the song’s success: “Its effectiveness was all Lil Jon. He took pride in the production.” True to form, “Blow The Whistle” is a mainstay at strip clubs, a fitting alignment given $hort’s provocative history.
Since 2006, $hort has released five solo albums and two collaborative albums with E-40. The longtime artist refuses to rest on his laurels. He also is one-fourth of the juggernaut Mount Westmore project, a West Coast supergroup that also includes Snoop Dogg, E-40, and Ice Cube. As he explained in our Dad Bod Rap Pod interview: “I have, in my files right now, like fifty solo songs that I recorded, that are Too $hort songs, mixed down and done. And then we did another fifty songs as Mount Westmore.”
In 2023, $hort had an Oakland street renamed after him, enjoying an honor bestowed upon only the city's most historically consequential figures. 2024’s Freaky Tales, a film set in 1987 Oakland, inspired by his song of the same name, furthered $hort’s relevance for a new generation.
Reflective and humble, speaking more as Todd Shaw than any of his larger-than-life personas, he exhales and considers his body of work’s lasting impact. “I’m lucky to still be here. I make way more money now than ever did in 1989,” he laughs. “The genre gained more value, we have more sponsors and we do these mega shows now, and that’s beautiful. I’ve been on this mission for a long time. The mission is: you can’t tell hip-hop what to do. You can’t tell guys like me from the West Coast [we?] weren’t allowed in the fraternity. I’m just thankful, man. And I just truly love hip-hop. I picked a damn good job."