How Copywriter David Burd Became Rap Star (and Hilarious Trojan Man) Lil Dicky

A Q&A with the rising star, plus his two new condom ads

Lil Dicky, the chart-topping MC, is back with more comedy gold for Trojan condoms.

David Burd, whose 2015 debut studio album Professional Rapper hit No. 1 on both Billboard's rap and comedy charts, anchored a clever, nervous, long-form PSA earlier this year, sponsored by the condom brand, about the dangers of unprotected bathroom sex.

Now, he's starring in two much slicker but plenty ridiculous new TV commercials, created with agency Colangelo, slated to first air this Sunday during the MTV Video Music Awards. (Trojan has a broader partnership with the youth-focused network, funding its how-to guide on sex and relationships.)

In the first new Lil Dicky spot, a :30, Burd and his date, Jen, can't keep their hands off each other as they arrive back at his apartment, making out in the hallway as he fumbles for his keys. Once inside, he scrambles to get a condom, while she—impatient in the heat of the moment—sweeps the contents of his desk onto the floor.

"Right here, right now," she says. Burd, baffled, launches into an eminently sensible sales pitch for protection generally, and Trojan BareSkin condoms specifically—but in a moment that can't help but evoke Larry David, also has to obsess over the mess she's made of his things. 

The second ad, a :15, picks up with the same scene, post-coitus, where Burd's rapid-fire neurotic patter is at full force right out of the gate, as he expresses relief that his paramour won't get pregnant, and proceeds to overshare about his gastric habits.

The commercials manage just the right balance of stupidity and substance, in a deliberate and entertaining enough way—it's a logical extension of the almost too obvious but ultimately perfect symbiosis between Trojan and Lil Dicky.

AdFreak caught up with Burd to chat about the new ads, his partnership with Trojan, and how, if it hadn't been for his pre-fame jobs at San Francisco agency Goodby Silverstein & Partners—first as an account executive on Doritos, and then as a creative on NBA—he might never have joined the rap game at all.

Read on to find out why—plus, which other brands he might like to work with someday, and the offhand origins of his own penile moniker.

AdFreak: How involved were you in writing the new Trojan ads?
David Burd: Pretty involved. I wrote it with this guy named Tony Yacenda. We co-directed the commercials, and he's directed a bunch of my music videos [including for the hit single "$ave Dat Money"], so we kind of wrote them together.

Your raps are known for drawing on your everyday experiences. Where did the concepts for these ads come from. Have you had a woman trash your desk?
No, I've never had this specific thing happen. But I imagine if it did happen in real life, I'd react similarly.

So, you were playing on that sort of movie cliché of a passionate couple coming in and knocking everything off.
Yeah, we had it feel like a really sexy thing, then transition into a more neurotic, the-opposite-of-sexy type thing.

To zoom out a bit, you've also recently appeared in advertising for Carl's Jr. and Madden NFL. Any other endorsements worth noting, or more coming down the line?
There are preliminary talks about certain things. As a public figure, I'm always interested in being part of brands that I actually enjoy. So, I would never do something with somebody I don't believe in, a product I don't believe in. There are so many products out there that I love, that I'd chomp at the bit to be a part of their campaign. But nothing really in the works.

Any specific examples of who else you'd want to work with, if you could?
I love Perrier. I don't know where they stand on advertising. But I'm happy to get in front of the camera and speak with complete confidence about how great Perrier is. There are probably so many more. I love the NBA. I love Nike. Nike is a great brand, obviously. But I also came from an advertising world, so I just enjoy the challenge of making a commercial. I used to do it. I mean, it's cool that I can do it now with way more creative liberty.

Anything else you'd share about how you choose which brands to work with—and what, for you, made Trojan a good fit?
Well, I certainly believe in safe sex. So, being on the right end of talking about that is something that interests me. And you know, I think Trojan is kind of the like the Michael Jordan of condoms. Even before I had the partnership with Trojan, and I would go into the condom aisle, I certainly gravitated towards Trojan, because it just felt like the most reputable brand, for whatever reason, whether it's packaging or just surface-level awareness or connectivity to it, it feels like the Nike of condoms, you know what I mean?

Did Trojan approach you, or did you approach them?
I met a guy [Dan Isenberg] who works for the company Colangelo. I met him through my rap career because he actually was a writer on a hip-hop blog [Complex]. And then he mentioned that he was changing jobs and going to Colangelo, and he mentioned Trojan, and I mentioned how much I believe in condoms and safe sex, and I think it happened kind of organically, conversationally. I don't think it was necessarily like me going and saying I want to be part of what you're doing, or them coming to me. It just kind of worked out that way.

Looking back further, how did your time at Goodby Silverstein & Partners shape you—both personally and in terms of how you look at working with brands now that you're an artist?
I don't know that I would've figured things out on the Lil Dicky perspective had I not worked at Goodby. I always knew I wanted to be a comedian my whole life, but I didn't have any sort of concept on how to make that happen, and I was pretty well positioned to get a job and not really take a massive leap of faith. So, I kind of felt like I had no choice but to really pursue a job, and I thought, you know, you're 20, why don't you try to find some sort of job where you're using your creativity? And I thought that [in] corporate America, advertising is probably the best approach to do that.

As soon as I got there, there were so many things that I saw. They have a whole wing at Goodby called eLevel. It's their production wing, and every day they're just churning out videos, content, whether it's internal, client facing, sometimes external, and it was very eye-opening to see how easy it is to make shit.

I was working on the Doritos account, and one of the things I had to do was give a report on chip sales, and it was a really boring Word document that showed how our ads were impacting the chip sales. But it went all the way to the head of the company, all the way to Jeff Goodby, so I thought, 'This is my one moment where I can interface with everyone important at the company. Do I really want to be boring, or do I want to take a risk?' So I made it into a rap song one time, and everybody really took to it. A) That moment [got me into] the creative department, which was a way better fit, and a better job for me, personally. B) I think it showed me, Wow, people really like your funny raps. Maybe in terms of being as comedian, this is an angle. Rather than writing a screenplay, or trying to make a sketch, what if you used rap as your platform, and [were] funny because of that?

It happened very naturally at Goodby, and I'm just not sure I would've figured it out if it didn't work out that way. It had a great impact on me personally and professionally in terms of being a rapper. It just all kind of fell into place that way. Then, once I started rapping more, I realized that I had this innate talent in me as being a rapper, even more than just being a comedian.

Once you saw your rap career picking up steam—be it early success like [your first YouTube hit] "Ex-Boyfriend," or more recently and significantly, Professional Rapper—did you think you'd be writing commercials again?
I didn't really think about it. I never sat down and thought, Could you be writing commercials again? I knew I wanted to be writing comedy, and acting in my own comedy. So, in theory I always knew I'd be doing something. I didn't know it necessarily meant it would be a commercial. I certainly knew I wanted to be writing stuff that I appeared in on screen.

But it helps having experience working at an agency. I'm just way more capable of talking to clients, understanding what we need, understanding what's overstepping my boundaries. I'm just so aware of the process, the way a rapper might not be aware when he's part of the campaign. I'm very much capable of being more than just a rapper.

But you also do enjoy, as you said, greater creative freedom … because you're bringing your own strong perspective and your own audience to the table, and brands want to be a part of that.
Yeah. Before, Dave Burd the copywriter was just writing stuff, hoping the client likes it. Now, whatever I like inherently has more value added to the client, because my opinion has clout that it didn't previously have.

Lil Dicky is essentially a brand in its own right, at this point. How did you originally come up with the name, and associated values, and how has what it stands for changed, if at all?
The name came [when] I just got my Macbook Pro when I was a senior in college, and all of a sudden Garage Band was a possibility. The first day I messed around and made some rinky-dink song, not at all thinking 'This is I'm going to be a rapper type thing.' But for whatever reason I just called myself Lil Dicky in that song, and I thought it was funny. It was a small penis joke. Lil Wayne was my favorite rapper at the time.

Then, two years later, when I'm sitting down deciding to be a rapper for real, I made a whole list of names in a Word document, and nothing really beat Lil Dicky. And I like rewarding organic, real moments like that. The reason I guess I liked it is because I kind of felt like it encapsulates sometimes the opposite of what you see in mainstream rap, of hyper-masculinity. You hear rappers literally talk about their dicks being so big, and it just felt like it was a cool way to show my point of view of not being the most hyper-masculine, 'Look at me, I'm a man' type of rapper. It kind of did that. And it stands out.

I don't know that the meaning behind it has really evolved, beyond my insistence on sticking with it. Because it is kind of a ridiculous rap name, to some extent … I really enjoy seeing it become more mainstream and common and accepted, because it means that the product is just that good. 

Check out Lil Dicky's most recent—and least humorous—video, "Molly," directed by James Less, below: