Examining How Lil Dicky Went From Making Funny Songs On YouTube To A Rapper With His Own TV Show Who Can’t Be Ignored

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In the spring of 2017, I was approaching the end of my senior year of college, where I had recently been informed a 2.2 GPA was good enough to walk at graduation. I was on cloud nine. I had about two more months of school left, but I knew a C- in my Econometrics class would be enough to get me to where I needed to be. (side note: Econometrics is the hardest class of all time. It turns out you can’t just walk in on the first day talking about “B hat” and “B star” and magically pass it).

Senior spring is the best time in any young person’s life. You’re an adult, and even though you’re still in college, school is essentially over. You enjoy it as much as you can; pushing the limits to the max because you know that in just a few short months, your life is going to do a complete 180 and you’ll be comparatively miserable for the rest of your time on the planet.

However, that two or three-month span is the most fun you will ever have. It’s like life says, “Hey, you worked hard for the past 20 years doing this bullshit ‘school’ thing. You deserve a nice break. Here are a few months of memories you’ll never actually remember. The only catch is you need to work at Geico for 40 years once it’s over. Deal?”

It’s a huge time for parties as well as the music that serves as the soundtrack to those gatherings, which will inevitably find a special place in your heart. Sure, you listened to thousands of different tunes during your time at school, but the songs that get played during the spring of your senior year will be ingrained in your head forever.

Whenever you hear these songs, you’ll be immediately transported back to the special moments you associate them with. “Roses” by Chainsmokers? Pregame at your house right before a verbal fight is about to break out over some pent-up “roommate isn’t doing his dishes” frustration. “Tennessee Whiskey” by Chris Stapleton? Sunday afternoon hanging out on the deck talking about the previous night and debating if “the pill” is necessary. “Love Story” by Taylor Swift? In my car with the windows rolled up and hat pulled down so no one can see me nailing every lyric.

You get the idea.

There is an emotional side to music and hearing any song that meant something to you in the past immediately gets you a little “in your feels.” It’s OK to cry—we all have—but the sad truth is there is no more college and that’s something that takes years to get over. No more waking up on a Thursday in March, skipping Econometrics (obviously), and getting a nice 24-pack just in time for the opening round of March Madness. Those days are long gone. Now you have to sneak an extra Chrome window behind an Excel sheet just so you can get the audio.

Everyone who’s played music in a room with other people knows there’s an unwritten rule that you put on a song everyone knows and likes when you have the aux in your possession. However, every now and then, people take risks. If you control the music, you have two options: play a crowd-pleaser or throw something new on with the chance of losing aux privileges (possibly forever).

Back in college, doing the latter meant you were taking a big risk, because while we all had similar tastes, putting on a new song that you vouched for but that turned out to be absolute garbage put a serious stain on your DJing privileges. However, as hosts of a good party or pregame, having a good mix of classics with a few new songs sprinkled in is essential, so we always tried to experiment.

And boy, am I happy we did. Do you guys remember Rob from the Dream Team Sitcom article? Well, not only is he great at hypotheticals but (whether he knows it or not) he changed my life one Friday afternoon in March of 2017. Rob was controlling the aux and decided to be bold and take a risk, knowing full well it could blow up in his face. Of course, as any good aux handler knows, when you put on a new song by an artist no one has even heard of, you turn down the volume to justify and explain what it is and why it’s being played.

“So, I just heard this song and thought it was pretty good. It’s called ‘Professional Rapper’ by some white dude named Lil Dicky. It’s also got Snoop Dogg. I listened to some of the other songs on the album and thought he was actually really good but this was my favorite.”

“Wow. ‘Really good?’ That is a bold declaration to say out loud,” I thought as I slowly leaned back in my chair and crossed my arms, waiting for the moment to pounce that never came.

Have you ever experienced a life-changing event that you thought nothing of at the time only to think back to that moment years later and realize it altered the projection of your life? That’s exactly what happened with Lil Dicky. Well, not really. It didn’t change my life or alter my projection (I’m still never going to try and be a rapper) but I did find my new favorite artist and I credit Rob for the assist.

It wasn’t immediate, though. I liked the song but forgot about it as the night went on. I had more important things to think about (Maddi was sending me weird signals, so I had to focus if I wanted to get her back. Maddi, If you’re reading this, please call me).

However, over the next few weeks, I would constantly find myself humming the tune in my head, and after realizing I had no idea what it was called, I texted Rob for help. This was a big step. This meant I liked the song so much that I was willing to passively compliment Rob and give him the satisfaction of knowing he found something I enjoyed. It doesn’t seem like much, but as a guy, it’s demoralizing. You don’t want to give anyone that credit—especially not your friends. You want to find everything on your own and show others. But sometimes you have to concede that you’ve been outplayed.

Once my memory was refreshed, I played “Professional Rapper” on repeat for a few days. I am an obsessive person, so when I like something, it’s all I fixate on until the next thing comes along. I played it all the time in my car, which eventually led me to his entire first album of the same name. This then led me to his mixtape, which subsequently led me to his social media accounts and it didn’t take long for me to learn his entire life story.

Over the course of a month, I became a full-on Dickhead. Not only did I like his songs but I found he was also talented in comedy, writing, and acting. He was creating an entirely new genre right in front of our eyes. I became obsessed with Lil Dicky and the man who is known legally as Dave Burd.

A white kid from the suburbs of Philly who went to a school very close to mine, was only a few years older, and worked at an ad agency making commercials before he said “Nope” to his lifestyle and locked himself in his room so he could make raps? If it wasn’t a true story, you wouldn’t believe it. He was my new favorite artist and it wasn’t even close (as pretentious as it sounds, I say “artist” as opposed to “rapper” because that’s what he is. He’s so talented in so many different areas that to simply call him the latter would be disrespectful).

If you’ve read this far, you’re probably thinking to yourself, “Wow, Tj is a fucking loser. This guy is writing a love letter to Lil Dicky for all to see.”

To that I say 1) You should be a Dickhead yourself 2) I get your point, it is kind of lame 3) I don’t care that it’s lame because I appreciate greatness. I am going to pen a public love letter to him in the hopes we someday have a Mac and Chase Utley type relationship.

So how does a frail Jewish boy go from Cheltenham, PA to signing on for the second season of a sitcom based on his come-up as a rapper? Well, I’ll tell you.

From what I’ve read, Lil Dicky has always seen himself as a star but he never knew exactly what medium would propel him into the spotlight. He grew up in a middle-class household, went to college in Richmond, Virginia, and then got a job at an advertising agency in San Francisco.

He was living the cookie-cutter life that would make any parent proud. He was following the tried-and-true 9-5 —> marriage —> kids —> retirement —> death lifepath and he absolutely hated it. His physical appearance would make you doubt this guy had any rhythm or flow but he absolutely had both. While working at the ad agency, he started to combine his comedic and rapping abilities to create funny songs that were also musically sound—sort of a combination of Kendrick Lamar and Weird Al Yankovich.

He was still working a day job in 2011 when he opted to stop going to the club on weekends and start posting up in his room by himself to write the raps that would serve as the foundation for his first mixtape. At the time, his friends thought he was crazy. Aside from some of the drunk “freestyling” that all white kids are guilty of, they’d never heard him rap. However, he was so confident and sure of his ability that he put the blinders on and continued to do his thing as they continued to live their normal lives, presumably mourning the loss of a friend who appeared to have lost his mind.

Then he released his first song. His family and friends urged him to not put anything on the internet because it was permanent, and they feared that if it bombed,  it would limit his ability to get a job. After all, you can’t rap about how your small penis stays “perched up on your balls” and then get an interview at Morgan Stanley.

He put it out anyway and their worries quickly subsided, as his first video got over a million views in just a few hours. It’s worth remembering this happen in 2013, and even though YouTube was a bit less crowded at that point, going viral was still impossible unless you were a cat or you had a brother named Charlie who bit your finger. However, Lil Dicky was able to do exactly that with “Lion King.”

He never looked back. His career took off, and in the seven years that have passed since he uploaded a song about a Disney movie, he has only seen his trajectory go up and to the left. (I don’t know exactly what that means but I heard it in a meeting once when I had an office job and I’ve always wanted to say it).

That wasn’t the only song to go viral, as he made videos for a few other tracks from his mixtape that also managed to get an impressive amount of traction.

People began to catch on to just how talented, funny, and extremely relatable (especially to middle-class white dudes) Lil Dicky was. His popularity grew with each video he put out, but unfortunately, his bank account did not. Sure, he could have realistically asked his parents for money, but the Jewish side of him could never do that (don’t cancel me; those are his words, not mine).

In the two years after the release of his debut video, he left his job and moved to Los Angeles to focus solely on his rap career. He was a starving artist with no income; an internet celebrity who was still confined to a shoebox apartment. He did, however, have a fanbase, so he made a Kickstarter and asked his loyal followers to help get his career off of the ground. He set the goal at $70,000 but almost doubled that, ending up with around $113,000 as Dickheads across the world took out their velcro wallets and helped him out.

It wasn’t just fans who took notice of his talent, as he managed to catch the attention of some other rappers—including one particularly legendary MC. In 2015, Lil Dicky’s debut album arrived when he dropped Professional Rapper on an unsuspecting world. It was his way of introducing himself to the game; to explain who he is and what he planned to do. It didn’t hurt that he got a co-sign from Snoop Dogg, which was an almost metaphorical “knighting” that sent the message this nerdy white kid shouldn’t be overlooked.

Snoop wasn’t the only notable name to appear on the album, as he also recruited Fetty Wap and Rich Homie Quan a year after the former blew up thanks to “Trap Queen” and the latter teamed up with Young Thug for the absolute sensation that was “Lifestyle.” That trio assembled on “$ave Dat Money,”  where he supplemented the song’s criticisms of excessive shows of opulence with a music video that was shot for $0, as he managed to secure a mansion, a Lamborghini, and some of T-Pain’s women at no cost to him whatsoever.

There was also “Classic Male Pregame,” a track about getting ready for a night out with the boys that hit almost too close to home.

He even managed to show he has an emotional side!

I’d also be remiss if I didn’ mention “Pillow Talking,” which features him addressing both sides of touchy subjects like religion and conflicts in the Middle East, all told through the lens of a one night stand.

These songs are what made me fall in love with a man. If you give them a thorough listen, I’d be shocked if you don’t also end up feeling a little tingly inside by the time you’ve made your way through all of them.

“Pillow Talk” also featured someone named “Brain” that no one had ever heard of because he was actually Lil Dicky’s alter ego. The character allowed him to dive deeper into his own mind and show off a different side, which was a pretty genius way to share some thoughts that are a bit more introspective than the ones typically conveyed by his more jocular primary persona.

Professional Rapper was Lil Dicky’s first album but it’s also his only official one to date (although “Brain” got his own seven-song EP in 2017, which shouldn’t have worked as well as it did). He has found the time to put out a couple of singles, one of which involves him switching bodies with Chris Brown and another made with the help of a star-studded lineup that includes Justin Bieber, Miley Cyrus, and Leonardo DiCaprio giving Earth some props for being dope. 

I don’t know if Lil Dicky has managed to achieve “mainstream” status but I think many of the songs I’ve talked about so far are fairly well known—which can’t be said for one criminally overlooked area of his oeuvre the hipster inside me is demanding I call attention to: his freestyles.

As anyone who has seen 8 Mile already knows, the best way to get “cred” that allows you to grow your “rep”  is to spit the hottest “bars” possible. B-Rabbit did this by battling at a rundown nightclub in Detroit, but nowadays, it’s primarily done by stopping by various radio stations and spitting as much fire as you can.

Lil Dicky has done this on a number of occasions, and every time he has, he manages to not just come up with unbelievably clever and amusing lines but also seamlessly weave them with whatever track he’s flowing over.

This clip of his visit with Tim Westwood is from a little earlier in his career and I played it endlessly back in the day. It’s full of quotable bars but there’s one in particular—”I’ve been skim milk chugging with a bitch hot as asphalt. Bitch wonder why I’m cumming quick, it’s your ass fault”—that really does it for me (even if it’s a bit too relatable).

 

His Sway in the Morning freestyle currently has 18 million views on YouTube and I’m pretty confident I’m responsible for around 500,000 of them. Every single line is perfect. It’s just joke after joke after joke. It all flows, makes sense, and hits you on a few different levels. The more you listen, the better it gets.

This clip from The Breakfast Club is actually from his show Dave (which I’ll get to in a second) and worth a watch just to hear him deliver: “Cause I’ve been working like a dog in this bitch, and that phrase doesn’t even make no sense cause dogs work probably the least of all the animals in the world.”

It sounds dumb when you’re just reading it, but once it graces your ears, you’ll understand.

With my inner hipster now satisfied, let’s pick up where we left off.

Thanks to his hugely successful YouTube career, album, singles, and freestyles, Lil Dicky was a bonafide star. He was boys with Bieber, hung out at Leo’s house, and probably even earned an invite to Little St. James that he vehemently turned down (which is a pretty sick flex in its own right)

By this point, he was living the real celebrity lifestyle he’d once only dreamed of and set out to realize another goal he’d always aspired to: getting his own TV show. It didn’t happen overnight, but thanks to his talent, determination, and personal relationship with Kevin Hart, he eventually landed one in the form of Dave. 

I could write just as many words devoted solely to Dave as I already have about the career of the man behind it but I’m very aware very few people would stick around for that if they knew it was coming. As a result, I’m going to do everything in my power to give it all of the appreciation it deserves in the concisest manner possible.

You could compare Dave to 8 Mile in the sense they both star an established white rapper playing an up-and-coming white rapper who is technically a fictional character but has basically the exact same life story and personality traits as their real-life counterpart. However, that’s really where the similarities end.

Dave‘s eponymous character hasn’t “made it” when we first meet him but is nowhere close to the “living in a trailer with your mom” level of struggle, as he sports around the same level of notoriety as Lil Dicky did when he took his talents to Los Angeles (where the show takes place) in an attempt to leverage his YouTube fame. Equal parts absurd and autobiographical, Dave provides an intimate look at what it’s like to be an awkward white guy trying to make it in the rap game and does so in hilarious fashion. 

There have only been ten episodes so far, and even though one or two of them might have been a little underwhelming, it was incredibly well-received and had the numbers to back it up. Dave averaged 4.8 million viewers per episode—2112% (not a typo) higher than the average number of people watching FX at any given time—and a second season is consequently in the works (which I’m prematurely branding a “must watch” based on what we’ve been treated to already).

I already showed you the freestyle on The Breakfast Club, which *SPOILER* is how the first season ends. However, the most impressive part of the entire season comes at the start of that last episode, which is when we’re introduced to the song “Jail.”

To provide a little bit of context, Dave and his manager are trying to convince a group of label executives to release “Jail” as his first single. Unfortunately, drama ensues after they fail to sway them—which may have had something to do with the fact that “Jail” is a 10-minute long track about a fictional journey through the correctional system.

The video is split up into four different parts but every single second is worth the watch.

 

So where does Lil Dicky go from here?  He’s currently working on his sophomore album, and as I mentioned earlier, he is taking his sweet damn time doing so. I’m not complaining, though. I get it. You can’t rush greatness. Do you think people were tweeting at Mozart and pestering him for his next symphony? Of course not. Good things come to those who wait, and based on how long we’ve been waiting, logic dictates it will be phenomenal.

As someone who’s been keeping an eye on the rise of Lil Dicky almost all the way back to the start of his career, watching his popularity grow has presented me with an interesting problem. You see, I’m a natural contrarian who instinctively looks for ways to hate everything that most people enjoy, but when trying to find something I don’t like about him, I came up empty.

Dave Burd is so talented that he transcends my intuition to dislike him out of fear of being labeled “basic” because I’m a fan. I’m not being even slightly hyperbolic when I say I think he is one of the most talented people to ever live. Am I delusional? Have I simply been brainwashed by the Taylor Swift for Dudes? Is this entire dedication piece a little much? Maybe. Whatever. Judge me all you want. I don’t care.

If you’re looking for more background on Lil Dicky and who he really is, check out this Whiskey Ginger interview with Andrew Santino, who co-stars on Dave as his manager. If nothing else you get to learn about his “penile surgeries” stemming from a condition he was born with called hypospadias.

You really do learn something new every day.


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