George Kase's 2007 new year's resolution sounded self-indulgent, like giving up dieting for Lent. "I will have more fun with my employees," pledged Kase, president of CCFC Advertising, a $20 million Chicago company. (That's him to the left, with the bird, surrounded by some of the people who work for him.)

He wasn't being frivolous. Kase, who co-founded CCFC 20 years ago, assumed the top slot in 2005 when one of his partners moved into strategic planning. The previous leader, who Kase describes as "a very business-by-the-book guy," had presided over a work-hard-play-hardly culture. Kase worried that employees were keeping late hours, rarely glancing up from their computer screens.

First things first: He enlisted freelance help and insisted the overburdened talk to him about getting relief. Second things second: He made serious plans to inject good times into the job. "I thought, we have to put fun on the agenda," says Kase. "I can't leave it to happen organically because it won't."

So Kase brought in some rubber chickens and a bag of plastic dinosaurs. He took the staff to a racetrack, held a winetasting and a potluck with exotic foreign dishes and chili dogs. He started asking everyone: What should we do? Where should we go? "I am thinking we might institute a duty roster where folks get to create and execute the fun on a rotating basis," says Kase. "Requirements would be that everybody gets to have the fun, it can't cost a lot, and it cannot impair the senses--too much--or be illegal."

Kase is not the only leader trying to reverse a fun deficit. Many companies start out fun, but the carefree ethos is tough to sustain through growth, hard times, and the constant flux of personalities. Too often, fun becomes something employees have everywhere but here. When once a year the leader pops out of her office and hollers "Frisbee toss!" the effort feels forced.

Some companies, however, do manage to keep the good times rolling beyond the holiday party, the summer outing, and the occasional carton of Krispy Kremes. To find out how, we surveyed close to 300 executives and interviewed many others. We found that business owners with (and this is admittedly subjective) fun workplaces have thought seriously about how play plays out in their businesses. We offer some of their thinking below.

Fun Like Me

Companies reflect their founders' ambitions, their values, and their personal styles. Not surprisingly, many also reflect their founders' senses of fun. More than three-quarters of the executives we surveyed said their personal tastes and humor influence the company's entertainment agenda.

That's as it should be--as long as the boss isn't oppressive. ("Bowl, damn you! Bowl!") So movie buffs run Oscar pools, rehash the weekend's releases every Monday, and occasionally lead an excursion to the cineplex. Outdoor enthusiasts take workers skiing or mountain biking and often locate their businesses accordingly.

That model works well in smaller businesses, where everyone knows the CEO and employees sign on to a leader as much as to a company. For example, it's hard to imagine that anyone interviewing at CGL, a $50 million logistics company in Downers Grove, Illinois, doesn't know exactly what he's walking into. CEO Dan Para loves golf, games, and gambling, and he loves them loudly. His three partners share those enthusiasms. The office game room boasts a 12-place customized card table emblazoned with the CGL logo; more than two dozen people may show up for Texas hold 'em on Friday afternoons (for money, of course). Signed photographs of Tiger Woods, Arnold Palmer, and Jack Nicklaus hang in offices, and the company hosts its own singles and doubles golf tournaments with trophies that migrate from one winner's office to the next.

Para's the kind of guy who talks a lot about butt-kicking; the politically correct gene isn't part of his code. CGL hosts a Fat Boy Open, in which its heftiest contractors take on a home team on the golf course; this year the four-man opposition weighed a cumulative 1,180 pounds. Some people must be offended, right? "Are you kidding? Here? No," says Para. "We play for $100 a hole and give the money to our family foundation. This year the fat boys lost $380." But Para has a sweet gene as well. Recently, on the spur of the moment, he asked the staff to vote on which employee they thought was nicest and most admirable. When the receptionist won, Para ran out and got her a $1,000 bond.

Someone Make This Place Fun--Stat!

Shockingly, not all CEOs are founts of levity. "I'm not an especially fun person," concedes Marv Shetler, founder and CEO of Blazer Industries, a $35 million maker of modular buildings in Aumsville, Oregon. "I participate. But I'm not the best person to plan things."

CEOs of a serious nature often rely on a "cruise director" (our term) to either formally arrange activities or informally stir things up. Close to a third of survey respondents reported that a life-of-the-party-type employee performs this role; only 3 percent said there was no such person at the company. At Blazer, for example, Kendra Cox--a project manager who is also Marv Shetler's daughter--organizes the holiday party, the summer party, and regular pizza soirees, among other activities. Cox is also an ambassador for fun, taking candid photos of her colleagues for display and personally inviting every one of Blazer's 220 employees to events. She distributes candy or customized magnets she has had made up as reminders.

George Kase certainly relies on contributions from his cruise directors. But he would rather see CCFC's wallflowers drive the new agenda. "Fun people are easily amused, so they're a slam dunk," says Kase. "If someone who is reticent socially has an idea, they're more likely to participate. If it's not stellar, maybe a fun person can riff on it and come up with something unexpected."

Laura Ricci, a consultant who helps clients win big contracts, endorses a variation on wallflowers: "wackos." Ricci, the owner of 1Ricci in Pewaukee, Wisconsin, may spend years embedded in a company, trying to shake up its culture. She finds that "cool ideas come from people on the fringe--creative souls who don't fit in very well." Ricci recalls one project for which she tried in vain to persuade a client's employees to update some databases. She sought the help of a guy widely regarded in the company as an odd duck. He first wrote a script for a voice mail broadcast in which he threatened to upend a box of kittens into heavy traffic if the updates weren't finished. Ricci nixed that. Then he composed a series of six e-mails, each in the voice of a different American novelist. "They were fabulous," says Ricci. "People were so captivated by them that they said, 'Okay. Okay. For you, I'll do it.' And they did."

Only 14 percent of survey respondents said someone in human resources handled fun, and some CEOs we interviewed scoffed at the very idea. Phrases like "too cautious," "not creative," and "sanitized" came up frequently. What HR staff does well is to note when morale is poor, many agreed. In that case, leaders should encourage them to tap others to get things moving.

The First Rule of Acting

Workplace fun often flows from the top down. But the best fun--the really fun fun--moves in the opposite direction. To encourage that, says Ricci, CEOs should follow the first rule of acting: Don't step on someone else's line. "In theater, there's a moment when the actor is about to evoke a reaction from the audience and another actor steps into the spotlight or talks too soon and ruins it," she says. "The jokes in your organization are probably already happening, and they'll get louder if you don't step on them." Kase agrees. In fact, he encourages his executive team to engage in irreverent banter in front of employees, to model how much is now permissible.

In all but the smallest companies, grass-roots fun is often specific to departments or other subgroups. Yet somehow everyone knows about it. At Blazer, for example, most employees can tell you about the pranks and wild displays of fandom that rage in an accounting department riven by loyalties to rival college football teams. Workers of a certain age squirm in apprehension of a visit from the Older Than Dirt Club, a group of women who leave black, leafless trees on people's desks to commemorate their 50th birthdays. Wandering around the parking lot at lunch one day, Cox discovered a small subculture of people who barbecue in the back of their trucks. "I don't know that you can create a fun culture," she says, echoing Ricci. "What you can do is not stop one."

Employee-driven fun often involves pranks: the office full of Styrofoam peanuts, the stapler that mysteriously empties itself every day. CEOs know they have a fun culture when the jokes are on them. Jim Haudan, for example, has been the butt of several elaborate pranks at Root Learning, his $20 million strategy-implementation and consulting firm in Sylvania, Ohio. On one occasion, several employees connived to convince Haudan that a top executive was leaving to appear in a movie with Katie Holmes. (The prank included an e-mail from the actress's real brother and a fake movie poster concocted for the cause.) Haudan tried to dissuade the executive, expressing serious doubts about his acting chops. The executive recorded this impassioned spiel, then played it before a howling audience at a company meeting. "I went for it hook, line, and sinker," says Haudan.

An exemplary instance of employee-driven hilarity is the "attack monkey," which has been cheerfully murdering people at AppRiver, an e-mail security company in Gulf Breeze, Florida. Three years ago, Hurricane Ivan ripped the roof off AppRiver's headquarters, forcing it to set up shop in a temporary location. To cheer the troops, software developer Erik Forsberg used a digital camera to film his sock monkey attacking another developer. Others pitched in on the film, and the staff was in hysterics as it made the rounds. Later, an administrative assistant decked out the monkey in a tiny red hood with devil horns.

Now when someone is hired, staff mull ways the monkey could attack, explains CEO Michael Murdoch. "We have a lot of funny people here, and I don't want to stifle that," he says. So far the 55-employee company has documented about 45 kills, including electrocution, strangulation, poisoning, and hit-and-run. The attack monkey finished off Murdoch during a job interview. It slid its salary requirements across the desk, and the CEO suffered a fatal heart attack.

Our Guys Are a Hoot!

Employees aren't just the best instigators of fun, they're also fun's best subjects (next to the boss, of course). Reality television grew fat on the entertainment value of the personalties and experiences of ordinary people. Ordinary people whom everyone knows are a richer vein of amusement.

Companies seem to get that. Among our survey respondents, mock talent competitions in the spirit of American Idol, So You Think You Can Dance, and The Gong Show were almost as popular as bowling. Another common diversion are in-house films that document workers just being themselves. At its holiday party, Blazer screens a video--including a blooper reel--that features reenactments of funny and peculiar happenings around the business. This isn't Farrelly brothers material: "We did a story about our plumbing department hiding a coffee pot that's not allowed on the plant floor," says Cox. But for Blazer employees in on the joke, it's comic gold.

Root Learning also celebrates staff at its end-of-year fete, honoring the employee with the most animated hand gestures, for example. But a more substantive appreciation of vivid personalities is a wall of employee caricatures in Root Learning's lobby. The day a new hire arrives at Root Learning, one of the company's graphic artists draws her. Over the years, details are added to reflect a growing familiarity with her tastes and quirks. In year eight, the caricature is decked out with a full array of personal effects and an appropriate background. Everyone knows the receptionist likes to change hair colors. Lest they forget, the drawing in which she sports a rainbow coiffure is a vivid reminder.

You Call This Work?

Arguably the Holy Grail of fun quests is making work itself entertaining. That's easy if your company produces board games, tougher if it produces boards. "People spend 40, 50, 60 hours a week doing something they don't like, and that's not healthy," says Ronald Culberson, a Herndon, Virginia-based speaker on bringing humor into organizations. "How do you make mundane processes fun? Aside from Southwest Airlines (NYSE:LUV), not many companies have managed it."

Employees left to their own devices may come up with ingenious ways to relieve the tedium, Culberson says. He recalls visiting one organization where administrative workers took turns opening vast volumes of mail. Every day, an employee not so engaged would place a small gift--a coupon for an ice cream cone, a comic strip, a candy bar--in an envelope and plant it among the rest for his colleague to find. In another company, clerks used stools, stepladders, overturned boxes, and the like to transform their file room into an obstacle course. "It sounds goofy," says Culberson. "But it made that process a little more interesting."

If you can't make discrete tasks fun, you can at least add excitement to the context in which they're performed. CEOs often fail to recognize cultural malaise because they themselves are on a perpetual thrill ride of wins and losses. Rank-and-filers, meanwhile, twiddle their thumbs in the ticket booth. Giving staff some numbers and teaching them to keep score gooses ordinary jobs with the frisson of competition. "Winning is fun," says Ned Compton, president of DEI, a 73-person Cincinnati company that designs and builds banks and other financial institutions. "We share sales and losses and financial performance with our people, and we explain what it all means. When we make a sale we all go down to our Santa Fe room and have a glass of champagne. They see the competition, and that's exciting."

Virtual Meeting Strategies goes further. Lots of companies build their financial periods around themes, but few do so with the creativity of Virtual Meeting, an Indianapolis facilitator of online communication. This trimester, for example, principal Neal Rothermel launched the theme "Big Picture" with a presentation in a movie theater that included popcorn and a preview of summer blockbusters. Another time, when the company had to execute a record amount of business, Rothermel declared the company to be "in Survivor mode." The executive team cleared the conference room and brought in tikis. Employees sat cross-legged on the floor. Everyone chose tribal names and wore headbands. For the rest of the period, tribes at each meeting would nominate survivors who had contributed the most or provided the best customer service. (No one was voted off the island.) "I wanted to find a way to share war stories across teams and celebrate above-and-beyond efforts," says Rothermel. "The returns on productivity and morale have been exponential."

And It's for a Good Cause

The first question CEOs ask when choosing philanthropies is "What best jibes with my mission?" The second question isn't "What would be the most fun?"--and probably it shouldn't be. Still, charities routinely build fun events into their fundraising. Companies can also have a good time doing good.

So what charitable work is fun? Runs and walks are great for the sinewy of thigh but are often held on weekends. (And we don't have to remind you that fun takes place on the company's time, not the employees', correct?) Anything collaborative--building a house, working side by side in a soup kitchen--can be fun. Helping children is often rejuvenating. DEI has adopted a class at an inner city elementary school. Employees take kids fishing and throw them a Christmas party, among other activities.

Jim Schleckser, founder of the six-person consultancy the CEO Project in Potomac, Maryland, observes that fun events are also a fine opportunity for CEOs to do some good for their companies by demonstrating servant leadership. "The CEO should be out there flipping the burgers, helping clean up, letting other people be the captain," says Schleckser. "But you've got to be the same person at the barbecue that you are the rest of the year. It isn't fun if it's not sincere."

Stephanie Clifford, Bobbie Gossage, and Athena Schindelheim contributed reporting for this article.