TORONTO – Nova Scotia rapper Classified has been a proponent of smoking marijuana for years, but he says Canada’s new legalization laws have left him confused over the ways he’s allowed to promote the cannabis lifestyle.He knows it’s within his rights to express his love for weed. And he’s allowed to talk publicly about buying shares of OrganiGram, an East Coast cannabis company he struck a loose business relationship with earlier this year.After that it gets a bit hazy, since most celebrity endorsements of a brand are prohibited under the Cannabis Act.“I was emailing OrganiGram going, ‘you guys know I’m actually an investor so we can probably get away with advertising more.’ I’m kind of curious to see what they’re going to come back and say,” he says, sporting a baseball cap emblazoned with a logo for the company’s first recreational weed brand.“They’re so careful not to cross that line. Almost to the point where I’m barely doing anything. I’ll bring them ideas and they’re like, ‘No we can’t do that.’”“I don’t even know what they’re paying me for. Like I’m wearing a hat, I’m trying,” he adds.Classified, whose real name is Luke Boyd, has been at the forefront of Canadian hip hop for over a decade, making him a valuable asset for young cannabis companies looking for prominent pot smokers. He’s worked with Buck 65, produced singer Ria Mae and swapped rhymes on a track with weed aficionado Snoop Dogg.The rapper also seems eager to test the boundaries of the new federal laws. His latest music video might even do that once Health Canada catches a whiff of it.“Legal Marijuana,” released Wednesday to coincide with legalization, features Classified standing with dozens of people in a public park as they rap along with his verses and every so often toke up and exhale a puff of smoke.That part of the video should be fine under the law.What might raise legal questions is a line he speaks that could be deemed an endorsement of a cannabis brand. The moment happens late in the video after Boyd adjusts his baseball cap and draws attention to the logo for Edison Cannabis Company, which is part of OrganiGram’s recreational pot portfolio.“Feelin’ just right, rollin’ up some of that Edison Reserve. Oh Canada, things have changed,” he says.The line doesn’t appear in the version of the song featured on his album “Tomorrow Could Be the Day Things Change.”If Health Canada views the rapper saying a specific cannabis brand has him “feelin’ just right,” it’s possible the regulator might see it as crossing the line as an endorsement, suggests Denes Rothschild, a lawyer who watches the cannabis industry.“If he has some sort of business arrangement with them and they’re paying him as an endorser… I think it raises a question,” says Rothschild, a partner at the Borden Ladner Gervais law firm in Toronto.“(The laws) are being interpreted and a lot of it is going to come down to where the government chooses to draw the line.”In an emailed statement, Organigram said it “was not involved in the production of Classified’s video.”“We remain committed to ensuring our brands and marketing practices are compliant with Health Canada’s regulations,” said Ray Gracewood, Organigram’s chief commercial officer.Representatives for Heath Canada didn’t immediately respond to questions about how music videos will be considered under the new laws.In the meantime, Boyd is willing to open the floodgates to potential business opportunities. After investing roughly $20,000 into shares of cannabis companies, he says he’s pleased with the upwards trend in their market value.“I’m not a big stock guy at all, I don’t take chances with my money,” he says.“But I’m making more on stock than I am on touring, probably.”Boyd’s perspective on legalization is tempered by a sense of caution over widespread acceptance. He worries about the “negative” side of weed, especially with parents who smoke inside the house while their children are present.“Hopefully people will be smart and realize it’s not good to just sit here and blow smoke in kids’ lungs and let them grow up with this type of lifestyle every day,” he says.At his family home in Enfield, N.S., just outside Halifax, he says it’s a rule that nobody smokes around his three pre-teen daughters. He typically lights up inside his recording studio.“I put in a different ventilation system so I can smoke, so it’s not going through my house every day,” he says.“But at the same time my oldest knows I use it sometimes and it’s no different to her than like, ‘Oh mommy’s having a glass a wine.’ OK, well daddy’s out there doing his thing.”In many ways, the rapper says legalization makes hardly any difference for him or his friends.“They smoke it like it’s been legal for years,” he says. “I think most people have.”Follow @dfriend on Twitter.