Picture a moodily lit Las Vegas casino, at first glance indistinguishable from any other pleasure palace on the Strip: salarymen hunch over $20 blackjack tables as waitresses with plunging necklines circle the floor.

Instead of bourbon-and-sodas, however, these waitresses are carrying trays full of vaporizers and water pipes. The games themselves have names that sound more like Cypress Hill songs: “Craps and Blunts,” “Roll and Roulette.”

High rollers, indeed.

A casino doubling as a smoker’s paradise may seem like a tired Cheech & Chong skit from the ’70s. But this vision is one of many ambitious concepts being hatched at High Times, the scruffy monthly magazine that, for 42 years, has served as the barely legal bible of dorm room stoners and closet cannabis growers.

Just as Playboy transformed from a skin magazine to a branding behemoth during the sexual revolution, a new management team at High Times is looking to pare back its outlaw image to become a lifestyle brand. Its big plans to capitalize on the era of legalized marijuana include a revamped website, apparel, furniture, nightclubs and eventually ganja-themed cruises, hotels and casinos.

“High Times isn’t just for historically self-identified stoners anymore,” said Larry Linietsky, a former executive at Universal Music Group, whom High Times hired in January as its chief operating officer. “We are appealing to everyone who likes cannabis, or is at least curious about it, both recreationally and for medicinal use. That could be your boss, your neighbor or even your grandmother.”

High Times, to put it mildly, is no ordinary media property. This is, after all, a magazine where the staff once smoked the founding editor (more on that later).

Started in 1974 by Tom Forcade, an underground journalist, drug smuggler and Yippie, the magazine was originally conceived as a parody of Playboy, but with lurid centerfolds of cannabis buds the size of bonsai trees instead of nude women.

Most underground publications of that era did not last much longer than the average Jerry Garcia solo. But Mr. Forcade, flush with cash from trafficking (talk about “seed money”), was able to keep High Times afloat long enough to find an audience.

It helped that Mr. Forcade, with his anarchist leanings, found a savvy partner who knew how to navigate the establishment: Michael J. Kennedy, a crusading New Left lawyer for the likes of Timothy Leary and Huey P. Newton (and later, uncharacteristically, Ivana Trump). Mr. Kennedy served as High Times’s general counsel and chairman before he died of pneumonia while being treated for cancer in January at 78.

Photographs | High Times Covers A lookback at some memorable High Times covers.

While High Times was all but invisible to martini-sipping straights, it had an avid cult readership. It featured paeans to pot by William S. Burroughs and Hunter S. Thompson, interviews with Mick Jagger and Bob Marley, reviews of the latest strains, tips for cultivators and smuggler’s tales from far-flung jungles. Among late-night doughnut scarfers, it was Vanity Fair, Consumer Reports and National Geographic, all rolled (oh, the puns) into one.

Even so, it was a curious media property. While there have been plenty of magazines that are outlaw in spirit (like, say, Thrasher, for skateboarders), High Times was the rare glossy devoted to a pursuit that violated federal law. As recently as a decade ago, High Times was sealed in plastic bags (as if it were Hustler) at Barnes & Noble. “High Times was pot pornography,” said its longtime publisher, Mary McEvoy.

Indeed, High Times lore is filled with stories that sound like old “Miami Vice” episodes.

In the 1970s, Mr. Forcade supposedly steered a recreational vehicle carrying nine tons of marijuana and $1 million in cash into the muck of the Everglades to avoid law enforcement.

When Mr. Forcade committed suicide in 1978, the staff gathered atop the World Trade Center (“so we could have the highest tribute possible,” one editor said), rolled his ashes into joints and smoked them.

In 2012, Matt Stang, an advertising executive, was charged with trafficking marijuana in a case involving the rap mogul Kareem Burke, a founder of Roc-A-Fella records. Mr. Stang, now 36, who paid a fine and received probation but no prison time after accepting a plea bargain, was recently promoted to chief revenue officer.

But in the current climate of legalized marijuana, those Wild West stories suddenly seem as dated as prog rock. America, you might say, has caught up to High Times.

Medical marijuana is now legal in 23 states, plus the District of Columbia, according to the National Organization for the Reform of Marijuana Laws, known as Norml. Adult use, commercial cultivation and retail sale is legal in four states, with several more, including California, likely to be voting on similar laws in November.

Along the way, pot has become big business. ArcView Group, a cannabis research and investment firm, recently called legal marijuana “the fastest growing industry in America,” having rocketed 74 percent, to $2.7 billion, from 2013 to 2014.

Attitudes seem to be changing just as quickly. In popular culture, potheads are no longer portrayed only as glazed-eyed dolts, but everyday professionals with children and mortgages. This week, Whoopi Goldberg announced that she was starting a line of female-focused cannabis products aimed at relieving menstrual pain.

In that light, the timing seems right for an underground publication once devoted to guerrilla-style cannabis advocacy to meet mainstream America head-on.

“We played defense for 40 years,” said Eleanora Kennedy, the widow of High Times’s former chairman, who maintains a significant interest in the company. “Now it’s time for offense.”

High Times subscribers who imagine the magazine being published out of a yurt in Humboldt County, Calif., may be surprised to see its actual nerve center.

The Midtown Manhattan headquarters of its parent company, Trans-High Corporation (T.H.C., get it?) is a warren of gray cubicles in a faceless office tower that could pass for a telemarketing firm.

The company’s new leadership seems equally corporate.

On a recent Monday, Mr. Linietsky was nestled into a white leather sofa along with the rest of the management team, wearing a white oxford shirt and brown blazer. A Wharton graduate, Cub Scout leader and former music industry executive who lives in Montclair, N.J., he may seem like a rebuke to High Times’s rebel heritage, but is an embodiment of the “canna-curious” consumer that the company is trying to court.

“I’m 44, and I can tell you, there are a lot of people my age who are going to a party Saturday night, and they’re bringing chocolates, vape pens,” Mr. Linietsky said.

What is clear to High Times executives is that there is money in the air, along with the blue smoke.

Take the High Times Cannabis Cups, weekend festivals with music, seminars, a trade show and celebrity appearances by the likes of Ice Cube and David Arquette. The festivals, which represented 80 percent of the company’s revenues last year, have grown to eight events a year, from one, and to more than 500 vendors, from 50. One event in Denver last year drew more than 50,000, who paid $50 to $420 (of course) for tickets.

The magazine itself is doing well. Despite a wobbly climate for print, advertising revenues have grown by double digits in recent years, management said, thanks to cannabis-centric brands like Kandypens vaporizers and Green House Seed Co. Issues have fattened to 160 pages, from about 130.

The editorial team recently brought in Will Dana, a former Rolling Stone editor, as a consultant to bolster its coverage of the booming industry.

“Twenty years ago, the magazine was relegated to covering small, secret grow rooms,” said Malcolm MacKinnon, the magazine’s editor in chief, who works under the pen name Dan Skye. “Nowadays, we see massive indoor and outdoor gardens, and people are begging us for coverage. We get multiple queries per day from companies seeking profiles in our pages.”

Its website has also seen a traffic surge; on a good month, it attracts more than four million unique visitors. The problem is that the site is blocked by many Internet filters, even on Amtrak. To rectify that, the magazine will soon unveil a safe-for-work spinoff that will swap out the bud porn for pot-themed lifestyle articles, including recipes.

High Times magazine’s 40th Anniversary cover.

Last month, High Times announced a partnership with Mashable to produce and share content on the politics and business of pot .

The next step in brand-extension is merchandising, moving beyond a few knit hats and T-shirts, to a wide array of clothing, accessories and even furniture. Flash a pair of High Times socks at the suburban cocktail mixer, and “it’s a little wink,” Mr. Linietsky said. “Now you’re in the club.”

Even so, a new line of High Times hosiery does not a revolution make.

Far bolder and riskier is its planned move into night life. While deals have not been completed, the company is deep in talks with partners to open a series of high-end cannabis-consumption lounges in Colorado, where adult use of marijuana is legal, and in Las Vegas, where medical marijuana is legal under Nevada state law.

In Las Vegas, the company’s partners have also secured a cabaret license and a gambling license as well as approval for an off-site dispensary at an undisclosed location 150 feet off the Strip, said Mr. Stang, the chief revenue officer. While the red tape is endless, this cannabis gambling lounge would provide a springboard for a potential High Times hotel and casino, following the model of the Hard Rock Cafe.

“We’ve seen brands transition from an outlaw brand to a mainstream brand — Harley Davidson comes to mind,” said Andrew Davis, a brand consultant in Boston who has worked with brands like the Jim Henson Company and Rodale, which straddle the media and consumer sectors.

But, he added, “a brand like High Times comes with a whole host of connotations that are sure to create challenges with zoning boards, City Councils, neighboring residents and local politicians.” To some civic leaders, High Times is “a magazine to be read in the shadows, like Hustler or Penthouse.”

Indeed, High Times had to withdraw its bid to hold a Cannabis Cup in Portland, Ore., last year, even after the state legalized marijuana for adult use, because the state liquor commission would not allow cannabis consumption in any place that served alcohol.

In addition, High Times 2.0 has gotten off to a rocky start. Two months after Mr. Kennedy died, David Kohl, a veteran media executive who was hired as chief executive in September, abruptly departed in a staff shake-up. (Neither High Times nor Mr. Kohl would comment on the move.)

Regardless, the upside is considerable.

“These are uncharted waters, but we’re talking about an industry that is going to be a multibillion-dollar industry,” said Dean Crutchfield, a New York consultant who advises corporations on brand-building strategy. “Who’s going to lead the category?”

Mr. Stang offered an answer to that question: High Times. “It’s the only real brand in cannabis,” he said.