This article was originally published on NahRight.com in 2015, just prior to the second leg of Lil Dicky’s Professional Rapper tour, and also as he was first starting to write his hit FX comedy series Dave.
Written by Daniel Isenberg
Lil Dicky ain’t your stereotypical Jewish rapper. Okay yes, he has a silly name. And yes, he’s a lanky guy from the suburbs with a beard. And yes, he makes funny songs. He checks all those boxes. But there’s one very important thing that separates him from the pack—he’s not wack. Watch his video for “Lemme Freak” once and you’ll instantly understand. Dude is legitimately nasty with the bars, an insane storyteller, a natural comedian, and a born performer. Stop fronting and give LD his props.
With the spring leg of his Professional Rapper tour starting this week, we got on the horn with Lil Dicky for our latest edition of The Green Room to get a detailed look at what life is like on the road for the blossoming rap star. Turns out things aren’t as glamorous as you might expect, though it sounds like that might change this go-around. Read below to find out all about Lil Dicky’s live show steez, in front of and behind the curtain.
First Live Performance
Lil Dicky: “In my case, it’s bizarre, because I wasn’t a rapper to the world until two years ago. I never really did anything until my first mixtape. So I put it out as a guy in his room making these songs on his computer by himself, and it blew up. And I was faced with the situation that I had to start doing concerts.
“Literally, my first concert was in my hometown of Philadelphia. I sold out the TLA which is like 1,000 people, and I honestly had never even rapped in front of more than like three friends. Ever. I would actually label that day as one of the worst days of my life. Obviously, it’s not a tragic day—it’s a good worst day to have. But in terms of my overall stress level leading up to the show, that day was pretty unbearable.
“After that first show, it felt like I was born to do it. It came very naturally to me. However, my biggest memory is for my first song, I walked out there, and I had so much energy that I went way too hard in the first minute and a half. And I got extremely tired. From that point on, the whole concert was an uphill battle to survive. I was rapping my verses like, ‘Just make it to the hook. Just survive this verse.’ And I did that for twelve straight songs. The stage was huge, and I didn’t know how to pace myself.
“But it was great. It was my hometown. Some 76ers came. Like, this is my first public foray into rap. I knew people were paying attention in my mind, but that fact that Nerlens Noel decided to come to my rap concert just felt like an alternate universe.”
“In between songs is really stand-up comedy-based. There are planned jokes. So what we mainly rehearse is the transitions. The songs just don’t end and then another one starts. Everything is driven by language. The rehearsal is less about me rehearsing my raps. Although, I want to do some more choreographed dancing. I haven’t done that yet. But it’s basically just making sure we’re all on the same page from a cue perspective.
“We put in like two rehearsal days before the tour. And then, you’re doing it every night which is like a rehearsal too, and then soundcheck every day too, so it just gets better and tighter as it goes on.”
“I’ve been working on my album, and that’s kind of been my sole focus, so I don’t even know what what my go-to on-stage outfit or what my look is for this tour. Since the tour starts tomorrow and I don’t know it, I’m gonna have to go with what I own.
“I’m less into basketball jerseys than I was before. And I can’t be in any sort of jeans or skinny pant up there. It needs to have air. Like, sweatpants or sweat-shorts are ideal, and those take up a lot of space. So I pack a few pairs of sweats, a bunch of hoodies because the hoodie is a great look on and off the court as a rapper. I pack a few choice button-downs that I would never wear on stage but that I would go to a bar afterwards in. And usually one or two pairs of shoes—I’m not a big sneakerhead.
“My big thing is that I have all of my bathing products sorted out. I bring a loofa, towels. I’m pretty anal about showering so I bring all my facewash. I make sure I have all that stuff at all times. I shower twice a day, and honestly, a lot of stuff that happens on tour is predicated around my showering.”
“Last tour, we got an RV and went four weeks straight without going home. This tour, I have shows Thursday, Friday, and Saturday night, then I fly back to L.A. and I’m here Monday, Tuesday, Wednesday. We’re doing that so I can finish my album.
“I like to rent movies on my iTunes, but then my battery dies. But honestly, there aren’t a lot of movies that I need to see that I haven’t seen. I’m at that place where it’s great when I find out there’s a great movie out that I haven’t seen.
“Usually I’m listening to rap music. At this point in my life, I only listen to rap. The new Drake, the new Big Sean, those are like what I flip and flop back and forth on currently. And Forest Hills Drive, the new J. Cole. I’m in need of a new one. I’m over those to some extent. I’m looking forward to Kendrick’s album, that’s coming out at the right time for me.
“In the RV, there was like a full bedroom, so I was able to have a bed. There’s a lot of weed being smoked. I actually try not to do it during the day, because it will just make me burned out and tired if I have a concert. But everyone else is smoking weed.
“I’m actually working on a TV show right now, which is based off of my life. It’s like Curb Your Enthusiasm, but instead of being in Larry David’s world, it’s in my world, and I’m a 26-year-old rapper. So I take heavy notes on what’s happening at all times on tour, and then try to put them together. I don’t really write the show on the road. I get all my notes done and organize my thoughts and think about things.
“I don’t think I could be in a moving vehicle and write rap music. I can barely even be in a studio. I need to be at my desk and locked in. I pretty much spent every day writing raps for the past year-and-a-half, and I started doing this whole thing to be a comedian, to be honest. I didn’t know I was going to become as good of a rapper as I became. So when I’m actually on tour, it’s my only time that I can’t focus on writing raps. So I take advantage of that time to focus on writing TV.
“That’s where my head’s at on tour, because when I’m on tour, that’s probably the most entertaining backdrop of my life. So I can imagine a lot of Episode 5 coming from that. Like, I have grown men coming up to me like, ‘Yo, can you sign my dick?’ Stuff like that is happening.
“I just say, ‘No. I appreciate your enthusiasm, but I can’t be the guy signing everybody’s dicks. I can’t be that rapper yet.’”
“I have friends who whenever I do a show are like, ‘Hey, can I come backstage?’ And I always warn them and say, ‘Sure, but it’s probably way more underwhelming than you’d expect.’ I haven’t been backstage at another rapper’s show, but I imagine it’s far more entertaining. Mine is really just four guys kind of sitting quietly. Half the time people are napping. I don’t really nap, I just kind of sit there.
“I used to never do anything in terms of drinking or smoking before went on stage. I used to just go on sober. Only recently have I started smoking weed before shows. I don’t do it every time, and I can’t go overboard. There’s been times where I’ve gone on stage high and it was too much stimulation to handle. I remember being on the first song, like, ‘Dude, please don’t collapse.’
“There’s usually dinner. A few menus being thrown at us, and then a conversation as to which type of food we should have that night. That’s what goes on, those type of discussions. It’s not like, ‘Oh man, Meek Mill just came through.’
“I’m open to change, though. I’m not absolutely sold on the current construct. And I think because it was it was my first tour last time, I took it seriously as a job. I was as responsible as responsible can be. But I think I’ll get more laidback in terms of letting myself have fun. My New Year’s resolution is genuinely to have more fun. There’s a lot more fun to be had. I don’t have any stories from my first tour to tell my grandkids that would blow them away. Even if it’s for my TV show, I just need to get out of my comfort zone a little more and see what happens.”
“I’m still educating people. There’s still a PowerPoint presentation in the show, which I always think is really funny. There’s hundreds of drunk people who came to hear rap music, and all of a sudden I take them through a 12-minute slideshow. I show them a deck. I say, ‘Before I get into this, I just want to make sure everyone is on the same page. I don’t know if you know this about me, but I have a little bit of a business background.’ And I get everyone’s minds in the same place for the show.
“I’m not sure if I’m gonna stick with it, but I have added the ‘Star Spangled Banner’ to my set list. An acapella where I get real Whitney Houston. I make everyone take their hats off. [Laughs.] I tend to go into the crowd and rap. I go down there, I gotta get with the people. So new things keep presenting themselves, then I keep assessing.
“I don’t know if I’m there yet, but the more money I get—I don’t really care about money—the more I’m going to invest in my show. In three years it will be a Kanye times Book of Mormon experience, hopefully. Imagine me on top of a huge mountain called ‘The Rap Game,’ and there’s chocolate milk pouring down the mountain out of what appears to be my butt, with strippers drinking the milk. It can go a bunch of different directions.”
Dry-Humping Girls During “Lemme Freak”
My favorite person I’ve ever seen live was Usher. And this is a trick I saw Usher do back in the day, when these R&B guys bring girls on stage and do a lot of dry humping. So I always wanted to have an excuse to do that. ‘Lemme Freak’ was the first time I ever wrote a song where I’m asking girls to have sex with them. I’ve never done the song live without doing that.
It’s never really gone bad, but there was one time that the crowd was so male dominant and the girls there weren’t really volunteering, and it took too long to get a girl on stage. It was weird, like I was forcing the issue. But it was funny how it took like 25 seconds to make that happen. Normally, girls scream and they want to do it.
In theory, I don’t ask her permission to do this before, so it’s a longshot, but you could see someone—if they really hated me—suing for sexual harassment. So I make it a point to whisper in their ear as it’s happening, ‘Are you okay?’ That’s my favorite part of the show, when I ask the girl if she’s okay. She’s like, ‘Yeah, this is cool.’ And I’m like, ‘Cool.’ [Laughs.]
“After a show, I’ll go by where I sell merch, and I’ll literally meet anyone who wants to meet me. So if the entire audience wanted to meet me, they would meet me. It takes like an hour and a half. People line up and it’s really fun.
“This is all so new, and I do so much of it by myself. Even now with my level of fame, I don’t really go out much or take advantage of it. My lifestyle isn’t any different than before I started. But when I’m here with all these people that are fans of my music, it’s like they see me as if I saw Denzel Washington, which is interesting to me. It’s so fun for me to meet people. I sign autographs, take pictures, and that whole thing.
“I want people to meet me and like me. A lot of me is reflected in the music, but I’m definitely Dave. 99% of the time, I’m not Lil Dicky. I want people to like Dave.”
Dream Female Tour Encounter
“After the show, I’m signing my autographs or whatever. Obviously, a beautiful girl walks up. And she’s not like the rest of them. [Laughs.] For whatever reason, I’m seeing a brunette. She says something like, ‘I had never heard about you until tonight when my friend…’ Basically, she’s not a huge Lil Dicky fan. She got brought there by a friend, and she just found out about it. So she’ll say, ‘I just found about about you. My friend brought me here. But I just want you to know I’m a believer, and I want you to know that I really appreciate what you’re doing and I think it’s awesome.’
“Then I’ll say, ‘Oh, thank you. What’s your name?’ And she’ll say like, ‘Kirsten,’ or something. I don’t know. And I’ll say, ‘Kirsten, do you live out here? Well, you’ve gotta tell me where I should be going next.’ And I’ll be able to know from that interaction if she’s interested in hanging out. Ideally, there’s a shower at the venue, and I say, ‘Kirsten, I think we should hang out after the show. Let me just shower real quick. Are you down to hang out for like fifteen minutes?’
“Then we end up going to some bar where me and Kirsten are really in our own world. It’s not that loud, and we’re just simply talking. She’s probably like 25, and she’s really confident. And I think it’s a situation where it’s the end of the night and everyone’s leaving, and I’m like, ‘Listen, I can’t leave now.’ I’m just kind of locked in.
“Ideally, we’d have sex. But that’s not what this is about. I think we could end up just talking. To me, when I watch movies and stuff, there are times when you meet a girl and you’re just blown away. I feel like that happens all the time in movies, but it never happens in real life. I’m waiting for that to happen. So I think this is an example of where it’s like, ‘Holy shit. This girl seems like she’s legitimately perfect for me.’
“I’d probably end up spending the night with her, and then try to get her to come with. She never will, because she’s got her own job and her own life. She’s got such an impressive life that she would never entertain the idea of doing that. But we’d stay in touch, and keep texting, and maybe it even turns into like Skyping every now and again. Then I’d see her when I’m back in town, and the connection is just as real. Maybe she moves to L.A., I don’t know.
“It’s not a drunk night where I’m grinding with a girl having the best sex I’ve ever had. It’s like a sober night, where it’s heavily conversation-based. And the first kiss is just as exciting as sex.”
Eating on the Road
“I’m pretty into fast food. I’ve got a bunch of fast food favorites. I’d say the Taco Bell/KFC combo is my favorite thing, because under one roof you’ve got great options. Chipotle is a great thing for me. I love Wendy’s—the Spicy Chicken sandwich has been a big factor in my life. Then, there are occasions where I’ll insist on going to Morton’s Steakhouse one night. It’s fast food, then every now and then there’s an unnecessarily nice dinner.”
Favorite Tour Stops
“My favorite show I’ve ever done was Madison, Wisconsin. All my shows before Madison seemed to be in major cities. Those are cool, but they’re not like a college town. The first time I went to Madison was the first time I was faced with a college crowd. And they just want it more. College kids go out every night with the sole purpose of having the best night of their lives. It’s really great. Everyone just buys in. So I’m really looking forward to going back to Madison.
“It’s my birthday on Saturday, and I’ll be in Utah. I’ve never been to Utah, so I’ll be spending my birthday in Salt Lake City. Maybe that will be cool. Actually, I’m looking forward to going to Indiana. I feel like that will be a very similar vibe to Madison. Chicago I’m looking forward to. I had never been to Chicago before, and after being there once, I think it’s a top 3 city in America. Minneapolis sold out like a month ago, so I think I have a really strong fan base in Minneapolis. Plus I’ve never been there. Going to places I’ve never been is great. It’s like, everyone’s seeing a PowerPoint presentation at a rap show for the first time, and I love that.”
Upcoming Tour Goals
“My goal is to have fun. The more I have fun, the more fun the shows will be. Beyond that, it’s just growing the fan base and connecting with the people I’ve never met. I think once people meet me, it will be even easier to be a lifelong fan. Then once the album comes out, I have different goals. But this tour is pre-album, so it’s getting people to keep spreading the word.”
The Professional Rapper Album
“I’m making it thinking that I’m going to get a lot of first time listeners. I know my fans are going to be into it, but I’m thinking about it from the perspective of people who haven’t heard anything. I think it’s great. I think it’s one song away from being truly tremendous. I think it’s still tremendous even if I don’t get that last song. But I’m always fighting for that last song, that cherry on top.
“I’m not gonna give anything away, but there are definitely some really cool features. And it shows off my diversity. My style is in the way I say things and my lyrics, but I don’t have a go-to sound. I don’t want to be limited to one sound. Also, before my music sounded like a comedian who could rap. But now, half my songs aren’t even funny. It sounds more like a rapper who’s funny half the time.”
After our NahRight interview, I became friendly with Lil Dicky’s manager Mike Hertz. And we ended up working together to bring LD to Trojan Condoms—a brand/client I was writing for during my early advertising days—for what would become a long-term relationship.
Here’s the first video we made with Lil Dicky and Trojan Condoms, titled “The Big Talk with Lil Dicky.” I love this so much, and I’m still so grateful I had the chance to work with LD and his team—they really are some of the most creative and talented people on the planet.
Special thanks to Mike Hertz for all of the above! And big congrats to LD for all the success! You deserve every bit of it!