There are a few reasons why we Love Lil Dicky. If you’ve never heard of him, get familiar. His persistence, talent and uniqueness is going to make you love him too.

Before we track his career, this is his latest song, good proof of his skills.


1. Lil Dicky is Daring and Authentic


Is he purposefully referring to his penis with his stage name or is he Lil Dicky because his real name is Dave? WTF is happening? I love the work of a grown man that refers to himself as Lil Dicky.


The fact that I cannot rid myself of my immaturities, understand the persona of hip-hop and now walk around saying, “I love Lil Dicky,” surprises me. But he is that good.


He is Jewish, and not in that Drake-Make-It-Look cool sort of way, popping bottles at a bar mixt fah. Lil Dicky is just as talented but far more true to his everyday Dave. He is this strange mix of weird Al and indisputable hip hop ability. What’s not to love?


Lil Dicky dares to be himself in an industry where everyone sounds like everyone else.


He reminds me of something Bruce Lee once said:


Always be yourself, express yourself, have faith in yourself, do not go out and look for a successful personality and duplicate it.


Lil Dicky is well aware that he is not what you expect and he isn’t trying to change your mind. He is trying to change how you look at a multi-billion dollar industry. As impressive as that is, it is not what I love most about this approach. I love that I actually believe he will do it.


Every rapper likes to say they are being themselves and keeping it real, but Lil Dicky is the first who doesn’t have to convince himself. You can’t fake his style of authenticity.   He sort of dares you not to like him, despite him being true to everything you have never expected from a rapper. I mean, I never thought the funny ones needed the talent of obliterating the competition.  


In an excerpt from the song, $ave that Money, Lil Dicky sings:


“I wear the same pair of jeans every day

Free sandwiches, homie, two stamps away

Book flight December but I leave in May

Drugs are generic but still work the same

I get logins for Netflix from my cousin Greg

Thanks, Greg!”



I hear this and I hear a challenge that roars, “I am who I am. I dare you to refuse me as hip-hop.”


He has figured out that no one wants to notice. Hip-hop is deeper than the materialistic surface that garners millions of views. You can get the same amount of clicks by being you. And Lil Dicky is authentic.


He is a prime example that hip-hop at the end of the day celebrates talent and a good story over shiny things. Because if it was all about rims and chains, the above-quoted lyrics would have been the reason for Lil Dicky’s exile. But here he remains, getting better and I predict, here to stay.


We should all be so fearless and committed to our work.


2. Lil Dicky works hard


Lil Dicky’s charm is obvious. We all appreciate a person who seems comfortable in their own skin, a person who doesn’t take themselves too seriously. But we also marvel at people who devote themselves to their work. Lil Dicky is an excellent blend of both virtues.


Yes, he talks about wanting to be the best. And the quality of his work proves his commitment. But listening to his songs and interviews, it is clear there is a grind he would rather show us than talk about.


And this is what I love about his work ethic above all else, it’s more show than tell.


Let’s take his music video, $ave that Money, again. The concept of it is to spend no money on a music video while making one, embodying the title. What I saw while watching the video was the desire of a man willing to do whatever it takes to get what he wants.


Before we take apart the less direct gems, let’s get over the obvious.


His level of creativity is astonishing. He is rapping about a concept while executing it. He even mentions saving money on the cost of his featured guest as his featured guest is rapping. The undertone of the song is that saving money is possible and entails a bit of effort, which he depicts brilliantly in cutscenes and his third verse. Almost every lyric is quality advice. Meshing these attributes is work but what is most intriguing are the underpinnings of what made the music video possible.


Lil Dicky displays the entire package of what it takes to be successful. It goes far beyond maximizing value while minimizing costs.


While being entertained, I saw a man that put his craft before his ego.


I cannot imagine walking up to the doors of strangers asking them for such ridiculous favours. I would be humiliated every time they said no. But Lil Dicky walked up to millionaires, asking if he could use their home for free. To shoot a rap video. You miss 100% of the shots you don’t take. Lil Dicky is ready to take every single shot available. Clearly.


I saw a man prepared.


I mean, just watch the video. If you can find a stone he left unturned then let me know. Because as he was making a free music video, he was recording a documentary about making the video. I hear the word hustle a lot in rap, this was the first time it was not vaguely addressing the entrepreneur in me.


He says in the song, “I am out in Cali, why is my company out in Delaware.” If you don’t know the answer to this, then …. Lil Dicky really covers all his bases, and it is time to do some catching up.


And it is not as if we end up with a half-baked product, the whole music video is a treat and a smash hit. He goes from venue to venue, failure to failure, favour to favour, and we get snippets of the successes packaged as an intriguing music video.  It is an excellent metaphor for achievement, except this time we do not get to ignore the sweat that went into it.


What’s More, most people are used to asking for help, but those whose generosity we seek do not want to do something for nothing. What is the solution? Huh, Lil Dicky? Explain how your benefit, benefits your helper.  


What is in it for them? Lil Dicky had a pitch handy, ready to quell resistance to efforts. It would cost him an extra twenty minutes of editing. People let him pretend to be rich and advertised a service/product of their choosing on his video.


He did all of this, while still being better than most rappers out there today. Lesson to learned? Give every inch of you to what you do.


3. Lil Dicky is intelligent and pays attention to details


Creativity is as complex as paying attention to the details that bring a thing to life. Can you find the right details that allow others to experience something that was once only imaginary? Yes? You sure? Congratulations, you are creative.


Your creation can be as simple as a stick figure or you can go crazy, making one of my favourite movies, Inception. The devil is in the details as they say.


How you move or place one detail can change the experience of your audience. Your intricacies are the fabric of your outcome. The quality of your details matters more than the quantity. But if you can achieve both, then you are the stuff of Lil Dicky.


The man seems to have a knack for the makings of a home run. He has found his space and hones in on the right details to convey his intent, every single time. This is an especially dangerous weapon for one who is not only self-aware but also in tune with his carefully selected demographic.


Take the music, Professional Rapper featuring Snoop Dogg, for example, a metaphor for the hip-Hop music industry and his introducing himself to it. He not only gives you the blueprint for his ascendance but forces you to take it seriously by so accurately depicting the issues of the current hip-hop landscape. From his suggestions of generic personas, to behind the scenes workings and all the way to the misogyny going on in corners almost out of frame, he gets it. You watch the video and watch a physical representation of Hip Hop culture. You listen to the song and hear his plan for it.




Lil Dicky makes every shot and lyric count. I paused the chalkboard scene of the video when Lil Dicky lays out a formula for becoming a successful rapper. There are actual details on that board that essentially serve as a napkin business plan. The audacity of the man! Showing his hand, knowing that no one else has the gonads to perform like he will.


And you can pretty much see a well thought out idea in every video he makes. His attention to detail is lives in every song. The man is not one for wasted space or energy. Lil Dicky goes as far as not just being unique but ensures that anyone who copies will be found wanting.


If you are going to do anything in life, you ought to strive to be the best. That entails knowing your work, inside and out. Having specific plans for your many objectives, to understanding your vision and the possible journey, while preparing for surprises. You need that habit of planning for your plans.


4. He is having a good time


Just because you are working hard does not mean you have to be a bore. Just because you have thrown you soul into tracing the rhythms of a beat with the elements of your self-expression, does not mean you have to be insufferable. Lil Dicky is making exactly these points.  


His work comes off carefree, almost a last-minute sort of vibe to his work. Except that what he does is phenomenal. There is no way he left any of it to chance. He is having fun but he isn’t stupid.


Example, his music video, and song, Lemme Freak, is technical, musical, clever, and especially funny. He gets buck naked. Not because he is leading a campaign to be your next Brad Pitt. The man is living life and loving it.


In the song, he takes you from meeting a woman in a bar, to the end of his life. The entire time he mocks himself, so well that I have to question if rap is not just a platform for his becoming a famous comedian. Every time he switches something in the song starts singing, starts dancing or shifts the tension of a character, the song gets more hilarious. There is a delight in his work.


You feel even further invested because you have no idea how the whole thing will end up. You laugh and enjoy his story till it dawns on you that he is talking about you too.


He lets himself go and is vulnerable. But he doesn’t ask you to cry with him, rather he seems to say, “my life is just as ridiculous as yours, why not laugh at me so you know you are not alone.”


In connecting with the energy that goes into his music, Lil Dicky asks us to enjoy a bit more.  Enjoy what you do and enjoy who you are.


My personal advice for getting this bit of Lil Dicky in your life? Find the work you love.  If you do something that makes you miserable, then aim for one that empowers you to fall in love with yourself. If you are not having fun, then reconsider. You either need to change your approach or start looking for something that lets you hang loose while you giving your all.


5. Lil Dicky has passion and Inspires


Once Lil Dicky has your attention, he earns it by making it worth your while. And he typically does this while holding your hand you through a story woven into a song. It takes a  lot of creativity and passion to be different as a rapper. Lil Dicky has done exactly that.


I am a new fan, still just combing through Lil Dicky´s music but so far I can say I have never come across a rapper like him. And being in the world of hip-hop, that is no easy feat. Take a gander at Lil Dicky’s body of work, how diverse and potent it is. Examine his rise to prominence, the traditional steps he took in an unorthodox way. Check out his freestyles.


“I must have wanted this really bad, I had something to lose,” Lil Dicky says. He could have gone the white collar route but he’d rather live fully, challenging and pushing his capabilities daily.  I see his work and I see the power of passion.


Lil Dicky inspires. At least me. He makes me want to do things my way.


I stumbled on Lil Dicky’s music by accident and my brain went a-buzzing. I kept mentally listing the reasons he ought to be considered incredible. I especially loved how the artist in him and the corporation are both evident in his song choices.


In doing what he does naturally, and me being so in awe, Lil Dicky gave me the idea for this series, Why I Love. I can’t wait to talk about more people I admire, discussing their attributes and what the rest of us may learn from them.


Lil dicky’s passion for his work inspired a journey in my own life, one I am sure he could not have expected.  And we all have that power. We all can be so true to who we are and our work that we give back to the world even when we don’t intend to. Let’s do that. Let’s be a little bit more like Lil Dicky.

PS. This is why I love Lil Dicky.




Brought to you by Bayo& Kristina