Lil Dicky is as unlikely a hip hop artist as you’ll ever find. But will the very things that set him apart trip up his path to stardom?

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It is almost noon, but it's unclear whether David Burd, a.k.a. rapper Lil Dicky, is awake.

"Hey Dave, you good?" his roommate-turned-manager Mike Hertz asks, knocking lightly on his hotel-room door.

Burd's muffled, somewhat hesitant voice floats into the hallway: "Uh, yeah."

The door opens and the 27-year-old is standing on the other side in a pair of blue boxers and a well-worn grey T-shirt, a bit of sleep crusted in the corner of one eye. The top of his head is covered in a mop of brown curls; his facial-hair pattern is more wildly overgrown scruff than intentional beard. He looks like a frat guy who won a beer-pong tournament: groggy, but not regretful of the previous night's events.

In 10 hours, Burd will take the stage at the Mod Club in Toronto's west end to perform his first Canadian rap show. He's found himself here, at a cheap hotel in Markham, (about 35 kilometres north of the venue) because Hertz found a good price for the room on hotels.com. The bonus is that way out here in the burbs, parking is free for their tour vehicle – an RV covered in a photo decal of mountains and an eager golden retriever. It, like nearly everything else about Burd, is the opposite of the traditional definition of hip hop.

Burd grew up in an upper-middle-class family in suburban Philadelphia. In junior high, he listened to the Goo Goo Dolls and attended Jewish summer camp. He studied business at a small, liberal-arts college in Virginia and graduated at the top of his class. He landed a job with an ad firm right out of college. And then he quit that job after the viral success of a music video he posted on YouTube in which he raps a verse about how intimidated he is by the size of his girlfriend's ex-boyfriend's penis. That video has more than nine million views.

Burd has emerged as one of the most refreshing but confounding voices in rap today. His two biggest hits satirize middle-class white-guy culture. Others, like his hip-hoppified Coles Notes of The Lion King, are pure Gen-Y bait. And then there's the odd track or two where he shows the sort of rapid flow and lyricism that suggest that under his funny-dude shtick is a serious soul. He wants to collaborate with the biggest names in hip hop one day: Drake, Kanye West, J. Cole. And with people like Diddy and Kevin Durant singing his praises, that dream might not be so far-fetched.

Problem is, some of the most defining things about Lil Dicky might trip him up on the path to stardom.

His name
In a genre populated by artists who call themselves Chamillionaire and 69 Boyz, it takes a truly absurd moniker to stand out. For Burd, Lil Dicky was the clear winner.

"There's value in doing, seriously, the opposite of what these rappers are doing," he says. "Being vulnerable and being real about your flaws and fears as opposed to being completely hypermasculine: 'I'm the man, I don't worry about shit ever.'"

Of course, Drake has already found mainstream success eschewing the hardness narrative, but Burd takes it many, many steps further.

His catchiest ditty, Lemme Freak, chronicles the story of him meeting a woman just before last call at the bar, trying and failing to buy her a drink after his credit card is declined and improbably convincing her to go back to his apartment where he has "some pizza plus a little bit of weed." He gets laid that night, but spends the next months in a relationship with the same woman, enduring dopey movies and inane conversations about the politics at her office in hopes that he will be rewarded with sex. The last verse flashes forward to the year 2074: The woman is now his wife, she has dementia, and she still won't sleep with him.

This is not Jay Z's Girls, Girls, Girls or LL Cool J's Doin It – when Burd is rhyming about sex, it's usually in the context of not getting any, or obsessing over the perceived inadequacy of his own anatomy.

If you ask Burd for a selfie, odds are he'll strike the same pose he always does: blank eyes, slack jaw, and holding up his hand with thumb and index finger just two inches apart: a physical representation of his name.

He may be too smart for his own good
Burd is on the stage at the Mod Club, downing what may be his third bottle of water for the night. He likes to wear the jersey of a local team in each city he plays in (tonight, in Toronto, it's R.A. Dickey – get it?), and this one is already soaked through. But the opening synth beats to White Dude pulse through the speakers and Burd senses he can take it a bit easier on this track, a fan favourite. Many in the crowd are jumping from one foot to the other as they recognize the song. If frat guys formed a sovereign nation, this would be their anthem.

Burd seizes on the crowd's excitement and pulls four white guys onto the stage who are all wearing some variation of the same outfit: a T-shirt, a baseball cap, relaxed-fit jeans. He sings: "But I'm rollin' with the top back, I ain't gotta worry where the cops at, I ain't gotta wear a fucking bra strap. Me and the crew are really doing everything that we like to. Man, it's a damn good day to be a white dude." The bros are dancing the way bros do: mostly with their arms. It is a strange thing to witness, these twentysomething men bopping along so emphatically and earnestly to this satirical song about white male privilege. They don't seem to be in on the joke.

Burd calls his fans Dickheads. Really. He sells baseball caps that say "Dickhead" on them. And people buy them and wear them at his shows, and possibly also out in public. There are dozens of young men, possibly hundreds, who have paid $25 (U.S.) for these.

Earlier that day, I'd asked Burd if his fans were who he expected them to be. He paused thoughtfully before answering, media-savvy enough to be careful with his words: "I thought they would be white men, so yes."

He's taking a big gamble
Burd tries to cultivate a slacker pothead vibe, but it's all an act. Sure, he smokes weed nearly every night, but he works hard – really hard – and is banking on the belief that input correlates directly with success.

After graduating from college, he got a job on the accounts side at the San Francisco ad agency Goodby Silverstein & Partners. The firm had the Doritos account and at a meeting Burd delivered the quarterly report in the form of a rap. A video of the unconventional meeting went viral at the company. After the firm's creative director Jamie Barrett saw it, it wasn't long before Burd switched to the creative side and was made a copywriter – a gig he left in late 2013 to pursue rapping full-time.

"There's this element of fearlessness that kind of blows me away about Dave," says Barrett, who has since started his own ad agency. "That he would go from an outstanding start, basically, as an advertising person to spending $10,000, I think, of his own money and starting to make his videos." The $10,000 wasn't savings from his ad agency job, by the way. It was bar mitzvah money – seriously. When he ran out of funds, he raised money with a Kickstarter campaign that attracted more backers than he'd expected.

That funded work on his first studio album and his first tour at the end of 2014, which had 25 stops.

The first tour was a success, but Burd says every dollar made on the road has been reinvested in the business. He's back on the road again now, on a 17-stop tour. Another leg of it will see him back in Canada in May and June. The first true test of whether this was a worthwhile investment will come when his first album drops later this year.

He doesn't care about money
Burd is not the guy whose mug you blow up to 15 feet in a Tag Heuer ad, or the one who reps an overrated brand of headphones. He wants an endorsement deal but only for the novelty of it. Stretched out under the covers of his hotel bed, scratching at his neck beard, he explains that a contract with K-Y Jelly lubricant would be so on-brand. "You can't get Dicky without the K-Y," he says, grinning boyishly at his own cleverness.

Success to Burd is measured in notoriety, not making the Forbes list of the world's highest-paid entertainers.

Last year, he posted a photo on Instagram modelling a pair of hole-ridden Old Navy boxer briefs that looked like they'd fought in an overseas war and then lived on the streets for a few months upon their return. He drives a 2002 Toyota Avalon, a mid-sized sedan – a grandpa car. In fact, the only reason he owns this vehicle is because he inherited it from his late grandfather. In a few years, he predicts, "I will be in a position where I can afford the Bugatti, but I most certainly won't be buying it."

Burd says his lack of interest in acquiring wealth is part and parcel of rejecting the traditional hip-hop narrative; but having grown up in an upper-middle-class family, he's in the position where he can reject it.

The way he addresses the role of racial inequality in hip hop has provoked a range of reactions. In October, Vice magazine printed a scathing character assessment of Burd following an interview with him, calling him "defensive" and "clueless." Burd maintains that anyone who is offended by his work is misreading the satire – and he says he doesn't want to defend it or explain it, either.

His ego
At one point during Burd's tour last fall, Hertz the manager noticed a Ford Explorer was following their RV. This continued for some time along the highway and Burd's imagination got the best of him. Expecting the outbreak of gunfire, he lay down on the floor. "I know what happened to Tupac and Biggie," he says. I'm not sure if Burd actually did this, but it seems to line up with the rapper's perception of where his own fame could lead him. He tells me: "I have Kanye's ego to some extent."

While he may be grounded in his lifestyle – the grandpa sedan, the penny-pinching – his career aspirations are sky-high."If I apply myself to rap, I'm gonna be the best rapper alive. If I apply myself to comedy, I'm going to be the funniest guy alive."

Those sorts of bold proclamations of his talent rubbed Peter Rosenberg the wrong way when he first met Burd last fall. Rosenberg is perhaps the most influential hip-hop DJ in America and exposure on his shows on the New York station Hot 97 can give any emerging artist a huge boost. As Andrew Marantz put it in a 2014 New Yorker profile of Rosenberg: "He has interviewed, mentored, or publicly harangued every living rapper who matters."

Aspiring to be one of the greats is a bit premature, Rosenberg says, on the phone from New York.

"I don't think one can be flippant at all about being, like: 'I want to be like Jay Z or Drake.' Especially if you've only been rapping for a year and a half. For anyone to say that – that's borderline like being, like: 'I just started playing basketball and I seem to be pretty good at it. I'd like to be Michael Jordan or Kobe Bryant.'"

There is one Lil Dicky track Rosenberg has played on air – notably, one of the few serious ones on the mixtape: Russell Westbrook on a Farm. While he is at times vulnerable and self-aware ("I've lived my life expecting love to come the second my attempt was done"), the track is ultimately about Burd's unflagging ambition and drive to rise to the top of this game he's just recently entered.

Is he a rapper or a comedian?
When he played in Toronto, Burd didn't begin his set with an energetic run of songs from his mixtape. No, that would've been too obvious, too standard for a rap show. Instead, he eased into the night with a PowerPoint presentation. With the confidence of a musicologist giving a TED Talk, he explained, at one point with a bar graph, why most rap shows are boring. He pledged to deliver a performance that approached the entertainment value of a David Blaine magic show (in his mind, the best entertainment available for purchase). While Burd worked the crowd that night, spitting catchy hooks with impressive flow, ironically, the PowerPoint presentation stood out as one of the most entertaining moments of it. It was a brief glimpse into how Burd could just as well launch a career in stand-up if he wanted to.

He chose hip hop as a vehicle to break into the field of comedy simply because it was easier than competing with hundreds of other aspiring comics in the club circuit, or trying to write a script for a film. Somewhat unexpectedly, he fell in love with rap – even when it was stripped of humour.

Rosenberg describes Burd as "skilled," and "really good for a funny-themed artist," but that's all he sees the rapper as for now. Being put in that box limits his chances at mainstream appeal, especially when the likes of Big Sean and FloRida are dominating the rap charts.

He wants to keep rapping for another 10 to 15 years, he says, and assumes eventually he'll run out of jokes. Introspection, though? That well will never run dry.

The question is, which version of Lil Dicky has a better shot of thriving: this supposedly more serious, more mature one or the guy who rhymes about his inferiority complex based on another man's genitals?

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Novelty acts

They were a pair of grade school buddies, in the throes of puberty, who usually dressed the same and tried to mainstream the backward-jeans look. It may have seemed that Kriss Kross was created in the wee hours by a group of punchy record-label execs, but in fact the two 13-year-olds were discovered by Jermaine Dupri at an Atlanta mall. After three albums and a failed attempt to break into the gangsta rap genre, they disappeared into obscurity, until the 2013 drug overdose death of Chris Kelly, one half of the duo. Their legacy: The infectious 1992 hit Jump, a wedding-reception staple.

One of rapper Riff Raff's earliest influences was king of novelty rap, Vanilla Ice, but the Houston rapper rose above his idol's one-hit wonder status and was signed to Diplo's label after spending years as a viral Internet star. Tip Toe Wing in My Jawwdinz, a single from his 2014 album Neon Icon, is filled with nonsense lyrics and an outrageous video that can only be interpreted as a send-up of the genre. L.A. Weekly once called him a "caricature of a hip-hop star," and with the long cornrows, lyrics about eating fried okra with Oprah, and extensive corporate tattoos (for BET, MTV and the NBA), the jury's still out on whether he's a parody artist or the real deal.

Afroman's Because I Got High, an infectious stoner ditty released in 2001, became an Internet hit before it was commercially released. But this novelty tune was taken seriously: It was featured in three movies and nabbed a Grammy nomination for best rap solo performance in 2002. That was the peak of Afroman's career, but he didn't stop releasing music independently in later years. His parody hip-hop Christmas album, Jobe Bells, features tracks such as Deck my Balls and O Chronic Tree.