Too Short: Rap Legend Talks New Album, Ageism in Hip-Hop and Why He’ll Never Stop Rapping

It’s impossible to overstate just how influential Too Short is to hip-hop culture. He is the only rapper to have worked with all of The Notorious B.I.G., Jay-Z and 2Pac, and over the span of his career, he’s dropped dozens of acclaimed projects. He is former Vice President Kamala Harris’ favorite rapper, and perhaps the only MC to have released albums across five different decades, starting in the ’80s.

While these are all groundbreaking accomplishments in their own right, the kicker is that the music is still awesome. On his latest project, Sir Too $hort Vol. 1 (Freaky Tales), his new records carry a youthful urgency, and include plenty of pockets where Short still raps like the rent is due.

“And out of all rappers since the beginning of hip-hop/ Who got more platinum albums than me?” he raps on “Check the Stats.” “And don’t count greatest hits, let’s go/ Jay-Z, Eminem, 2Pac, OutKast, Nas, Drake, Lil Wayne, Kanye/ Who got more platinum albums than Too $hort?”

The answer is: nobody. Considering one of the biggest records of his career — “Blow the Whistle,” which turns 20 next year — didn’t pop off until Short was 40 years old, he’s long been known as someone who probably has a smash hit still tucked away in his back pocket.

“How long can a rapper rap?” Short asks Billboard. “How long can a rapper rap and release relevant music? To what age is it appropriate to rap on stage and actually put on a good performance? What are the limitations of hip-hop? It hasn’t been written yet.”

Short will be turning 59 next week, and he openly discusses his age on his latest album, flexing it like a veiny bicep after a good pump. “I thought you knew, I’m still rappin,” he spits on opener “Still Mackin.” “I thought you knew, b—h, I’m still mackin’/It’s the 2020s and I’m still rappin’.”

Short spoke with Billboard about his new album, ageism in rap and what it felt like stepping into the production chair for the film Freaky Tales.

“I won’t stop” are the first words uttered on Sir Too $hort Vol. 1. You’ve had an unbelievable career, but do you ever feel pressure to stop rapping because of your age?

That ageism is biased on both ends. ‘Cause the older guys think that the younger guys aren’t skilled enough to be in their game, and the younger guys are like, “C’mon OG! It’s my turn.”

I’m comparing my activity to B.B. King and The Temptations — like, people who aren’t in my genre, that went well beyond their senior citizen years and kept performing and satisfying audiences. I’m not measuring this towards other rappers, because rap has not all the way gone there yet. When it’s all said and done I would love for a younger rapper, just one, to say, ‘Man, I wanna stick around like E-40 and Too $hort’. Motivation!

The ageism is there — but at the same time I’m in that battle of just making the narrative. This is what I’m doing, and nobody in there is dictating what it should or shouldn’t be. It’s just me figuring it out.

It’s been five years since your last album, a notable break for you. What inspired this break and why did now feel like the right time to get back in the studio?

I make a lot of songs, and a lot of the songs I make are really good songs — I just haven’t been releasing them. Sort of because of how the industry is. Like, are you gonna be independent? Are you gonna try to get a deal with a major? What’s gonna happen with the marketing and the singles and stuff? It just changed a lot from the OG way I used to do it — and then the results I would get, I wasn’t really feeling like I needed to prove anything.

How has your love for hip-hop deepened over the years? What about the artform keeps you here at almost 59 years old?

It’s just painting pictures. I think I have some of a pre-music video mindset approach to writing songs. When I say pre-video, I mean everything before MTV, where you listen to how songs were written and a lot of songs before videos were made, you actually see a picture when you listened to the song. You see the movie, you see the scenes, because they’re explaining it to you in such a way that there’s no need for a film. It’s songwriting! I like to write visual songs, and I’m a part of that old guard.

What are your thoughts then on the use of social media and TikTok now? For someone who’s been around since rap’s early days, how are you feeling about the state of the genre now?

I’m jealous of the new artists! I’m jealous of the tools they have and opportunities they have. What you can do with popularity now was definitely not available to me, and definitively the tools to market and even make music were not available to me, either. As in sports, you have to survive your era. You have to be on the top of the game in your era, whatever that is. Just maximize it. I’m very curious to see where [hip-hop] is goin’, in a positive way. I know it never stays in one place and I think hip-hop is in good hands — because as a business it did not collapse. A lot of people come in the game every year and get a lot of money, and if they weren’t, I would say it’s a problem.

How are you feeling about West Coast music right now, specifically?

When you have artists that continually break out, fom the G-Eazys to the YGs and Kendricks, you’re proud of your region. As the OG’s, when our youngsters emerge we have to support them, and we do that. The West Coast is a unit that rides for each other. I think the state of West Coast rap is wonderful. One of our guys just survived something nobody else has ever survived, and that’s an onslaught from Drake.

“Blow the Whistle” turns 20 next year. Tell me about how you feel about that record now.

It’s like a parent who has three, four, five kids — and you clearly love one of your kids more than the rest. It’s that kid. You can’t even hide it. I made that song when I was 40, I’d already had multiple platinum albums and gold albums — and it turns out [“Blow The Whistle”] is gonna be my signature song. You couldn’t find one artist who strung a bunch of top-selling albums together in a row and after making all of that albums made their signature song. Nobody did that. Zero. Zilch. Nobody. That’s a Too Short thing!

What was the recording process like? Did you know it was gonna be a smash?

I can’t say I can pick hits. I don’t know how to pick hits, not yours or mine or anybody’s. I feel like that’s a jinx, to name a song a hit before it leaves the studio. “Blow the Whistle” was originally made in 2005. Lil Jon produced it and he was really into Crunk Rock at the time. “Blow the Whistle” — at some point there were rock guitars that were added to the song, and when it was mixed and mastered it was mixed with the guitars. I had a conversation with Jon about not using the guitars, and he’s like, “Nah man, that’s hot!” He assured me the new way with the guitars was the best way. So I just went in the studio and muted out all the guitars and that’s the version we all know and love.

Was Lil Jon upset?

At some point — after a while, he came and said, “You won this one.” We had disagreements in the studio prior to that where he would be right. He held his opinion firm — and I don’t know if he felt some kind of way for a while, but when it was successful, those feelings went away. I do just wanna add that my next album, Sir Too $hort Vol. 2, is 100% produced by Lil Jon.

How did you get into the producing chair for Freaky Tales?

It didn’t take me long to say yes. I read the script before they did any filming. I knew about the chapter that was focused on me. They were asking me to, “Please attach yourself to this project,” and I was like, “Please attach me to this project!” It was mutual. At some point, they fit me in the script as the narrator. I don’t even know if that was their plan or not, and they gave me a cameo. It’s an Oakland movie, shot in Oakland, named after one of my songs. I’m on Cloud Nine right now, bruh.

To add to that, you were also put on the bill for the Rock the Bells Festival. How does that feel?

Oh you just told me, I didn’t even know, s—t. I consider myself 100% to be part of the Rock The Bells family. The motivation for the people over there is really just to uphold the legacy of hip-hop and to not let you forget, and I’m just really proud to be a part of that. I receive a salary for the [radio show] I do, but I promise you I do not do that show for the salary. I do it because I really signed up to be a part of what LL Cool J is preaching over there.

LL was very, very arrogant and very unapproachable as a young rapper — but as an old rapper, OG rapper, he is a hell of an ambassador. Open heart and a whole different L. He played his rap persona to a T… but now It’s nothing but love to all of hip-hop.

Next year will also mark the 15th anniversary of Wiz Khalifa’s “On My Level,” which I feel like introduced a whole new generation of Too Short fans.

That was another one of those bridges. I’m an OG rapper in ’05, ’06 and I’m just riding my wave. I’m out there doing what the game gives me and another bridge comes along. It turned out to be a song because of the new look it gave me, I used to open my show with that song! It would reel the crowd in. I love Wiz for that man. He put me on a gooooood song.

What are some tips you have for younger artists that wanna have longevity like Too Short?

I think loyalty in this game has a lot to do with longevity. Sticking with the people who are really your friends that you started with, who really know you and love you and tell you you ain’t s—t — cause at that moment you really ain’t s—t. I think a lot of our young artists are turned off by the industry because it’s not instant enough, it’s not Folger’s coffee. The one’s who are supposed to be here will be here, cause they’ll endure.

Everybody that’s had a long career, it wasn’t just one long run. Big f—ing dry spots in the middle where you gotta figure it out. Big moments of doubt. The crossroads come, I wouldn’t say often but they continuously come and when you stand at that crossroads you have options. So you might make a wrong turn. So what? Find your way back on track.

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