It was nearing midnight as Dwight Cleveland rubbed his eyes and blinked hard. His body ached; his eyes burned; but the thrill of the hunt kept him going. Under sterile fluorescent lighting and kneeling on cold linoleum tile, Cleveland had spent the last 13 hours in this cramped Japanese poster shop recessed a few steps below a seldom-traveled alleyway in Osaka. It was there that he had scrutinized every two-paneled film advertisement in the store’s seemingly endless array of 3-foot-tall stacks of inventory. In a way, it was as if Cleveland had not only traveled more than 6,000 miles across the world, but also back in time, for the shop’s decor—including the most eye-catching posters that Cleveland had uncovered during this marathon shopping session—reflected the Swinging Sixties.

According to the 52-year-old collector, when it comes to American films, oftentimes foreign posters boast the best artwork. And when it comes to James Bond films, only one actor perfectly encapsulated the role. That distinction belongs to Sean Connery, and Cleveland, who owns Connery-specific James Bond posters from 15 countries, declares that the Japanese examples are beyond compare. "The Japanese got it right; they’re the best of any country," he says. "I own a ton of Japanese posters and by far, my favorites are the James Bond ones. They nailed Bond."

As the shop’s clock ticked into the wee hours of the morning, Cleveland wrapped up his search. As he would later explain, "since this was a target-rich environment, I knew I had to stay and dig through absolutely every single scrap of paper." He was ready to purchase almost 1,000 posters—"the mother lode," as Cleveland describes it—and his next task was to arrange a method of payment and shipment back to the United States. The trouble was that Cleveland spoke no Japanese and the shop’s owner spoke no English. After a laborious day analyzing every poster in the shop, which incidentally came at the end of a whirlwind trip during which Cleveland had traveled the entire country by train, he was not about to be deterred by the lack of a common language. Eventually, through the use of simple pictures, dates, and times, Cleveland communicated to the shop owner that he was flying home from Tokyo in two days, and he arranged a meeting with the owner at a Tokyo hotel where he would pay him the $30,000 that the posters were worth. "If you’re motivated, you can always communicate," he says.

But, as Cleveland also will tell you, anything can happen when it comes to international poster collecting. "When I got to the hotel [two days later], I had everything covered," he recalls. "I was on it like a wet blanket." Except that the staff at the hotel where the shop owner was staying had no record of his name, despite the shop owner’s business card that Cleveland produced. In a panic, Cleveland called a Tokyo-based poster acquaintance and discovered that the Osaka shop owner was a famous female impersonator and was known by his real name only in Osaka. Evidently, the shop owner had checked-in to the hotel using his stage name, but it was a name that Cleveland didn’t know. Because his flight was quickly approaching, Cleveland entrusted his acquaintance to track down the shop owner and make the exchange on his behalf. And so, Cleveland flew back to the United States $30,000 poorer and without a single poster to show for it. One week later, however, Cleveland’s shipment arrived in Chicago in perfect condition.

While such an incident would intimidate some, that adventure, which took place in the fall of 2001, further energized Cleveland, and he made numerous return trips over the next few years. During those trips, though, Cleveland made sure to hire a translator. "Over a two-year period I bought everything that I wanted in the entire country of Japan," Cleveland says. "No Americans had owned any [Japanese movie posters] at that point, so I’d just go into these stores and would buy these things for nothing. It was like bobbing for apples."

Cleveland’s love affair with classic movie posters can be traced back to the spring semester of his senior year at the Brooks School, a boarding school located 30 miles north of Boston. Cleveland’s dorm parent, Mike King, was the director of the school’s art department, as well as a passionate collector of film posters. One evening Cleveland happened upon King as the teacher was returning from a trip into Boston, where he had purchased a handful of lobby cards, including one for the 1929 film The Wolf Song, starring Gary Cooper. The moment Cleveland laid eyes on that 11-by-14-inch lobby card, he was hooked. "The start of my collecting was really falling in love with the Art Deco graphics and the color saturation used in those early 1920s and 1930s posters," he says.

From that point on, Cleveland was determined to acquire The Wolf Song lobby card from King. But as he recalls, "In the early stages of this hobby, these posters weren’t bought and sold; it was trading paper for paper. It really wasn’t about the money." Cleveland had a list of other posters that King wanted and he knew that if he could procure them, he might entice King to make a trade. Over the next year—a year in which Cleveland interned for a state senator in Los Angeles and later, another politician in Washington, D.C.—he frequented the poster shops on Hollywood Boulevard, as well as those in less publicized locations, and quickly discovered "incredible inefficiencies in the market." Finding posters priced at $5 or $10 in obscure shops that were being sold for $100 in the Hollywood Boulevard galleries, Cleveland could speedily turn a profit, and he established a core of classic posters that would prove to be valuable trading commodities down the road. Then, in Washington, D.C., Cleveland met an enthusiast who was selling the remnants of his collection. The dozen pieces included three posters from the Marx brothers’ classic 1933 comedy Duck Soup, which was a film on Mike King’s wish list. Cleveland dropped about $275 for the 12 posters and soon made a trade with King to acquire the elusive, 1929 lobby card he had first seen as a high school senior.

King was anything but surprised. "I was excited at the possibility of getting some of those posters," the 77-year-old recalls. "But I wasn’t shocked. Dwight’s one of the most focused people I have ever met, and that’s a great thing to have if you’re going after posters."

"He could strike a hard bargain," King continues, speaking of Cleveland and his resolute ways—a character trait that he possessed even as a teenager. "When he wanted something, he would go after it 100 percent, which is a good thing. That’s what makes him what he is today. He’s one of the leading collectors."

Around the time that Cleveland made his trade with King, the thrill of the hunt had transformed him and he soon amassed his own collection, though he says he never approached movie posters like a typical collector. According to Cleveland, most collectors first have an affinity for an actor, a director, or perhaps a specific movie or genre; their interest begins with the film, which leads to an interest in the poster. Cleveland’s interest, by contrast, always began with the poster. The film was a secondary discovery. "I fell in love with the artwork first, and it was only after that that I learned to fall in love with the movies," he says. "Not everything that I like is the most valuable. Some of my favorites are movies that aren’t famous at all and don’t include anyone famous in them."

For Cleveland, the best movie posters are the ones with artwork that does more than advertise a film; it communicates the film’s message. "You see the poster and the whole film comes to life," he says. "Those are the posters that have become the Holy Grail for me. On one piece of paper it communicates a greater message that took two hours to communicate in the film itself. Those are the ones that are the most special."

The hobby of movie poster collecting changed significantly—and many believe for the better—when Christie’s hosted the first sale devoted solely to film posters in 1989. Prior to that, avid collectors like Cleveland were relegated to conventions in the basements of downtrodden hotels positioned near highway exit ramps in uninteresting areas of the country. But when the major auction houses began devoting attention strictly to movie posters, the world took notice. Collectors were granted a newfound legitimacy to their obsessions, and values quickly skyrocketed. "All of us in movie posterdom would descend on New York and it was like this poster orgy where the dealers were open crazy hours and we would be cutting deals and buying things at auctions," Cleveland recalls. "It was really great."

But with greater publicity came greater competition, and to stay ahead of the pack, Cleveland often had to outthink his fellow bidders. For example, when John Kobal—a Hollywood historian who penned more than 30 books on the subject, including 50 Years of Movie Posters—died in 1991, his personal collection of posters was auctioned shortly thereafter. The auction took place in London only a day or two after the annual New York auctions and conventions, and knowing that most of his competitors would arrive in London just in time for the sale, Cleveland made sure to take the earliest flight out of New York that he could catch. That assured him the time to preview the collection before each item crossed the block. By doing so, he learned of a Lady by Choice poster (a 1934 film starring Carole Lombard) that would be pulled from the sale due to its relatively poor condition. When the auction ended, Cleveland inquired about the poster, paid a nominal price, and later boarded a plane back to New York with a poster that he says today is worth about $15,000.

There are few places that Cleveland hasn’t visited to buy posters; and some stories from his years of collecting are so implausible they seem better suited to the plots of the films represented on his posters. For example, upon hearing about a home in Michigan undergoing a major renovation where lobby cards were found tucked inside the insulation and studs of the walls, Cleveland quickly visited the property to examine the findings and potentially make an offer. He estimates that he bought about 8,000 posters from the homeowners during that trip, and because there were so many duplicates, it was difficult for the homeowners to contemplate what they might be worth. In the end, Cleveland made a significant profit, selling one poster the following weekend for three times the amount he paid for the entire lot.

However, in those circumstances Cleveland isn’t out to scam anyone. He may have walked away from that acquisition with a great deal, but he let the homeowners name the price. "There’s a delicate dance that goes on and that’s where the poetry in the acquisition is," he says. "Because of that, my main method is to say to people, ‘This is yours; you own it. It belongs to you. You know what you’ve invested in it and you know what you want to part with it. I’m here with cash and I want to walk out the door with it.’ It’s easier for them to pick a price and I can either agree or disagree with it."

Cleveland’s other major strategy is one that he learned early on from a fellow collector. He was advised not to become a dealer. While a dealer has the advantage of a brick-and-mortar location where fresh merchandise can come in off the street on a daily basis, it’s also restricting because significant time must be spent at that location. Instead, Cleveland invested heavily in advertising, taking out about 50 ads a month in various domestic and international publications. Those ads provided him with fresh leads (much the way a dealer would acquire them through store patronage), but he still had the freedom to travel and to devote time to his primary business as a real estate developer.

Finally, Cleveland has succeeded in large part due to good foresight and an entrepreneurial spirit.

"If I went into some place and there were many copies of a poster that I loved and believed in and knew that it was undervalued, I’d buy all of them," he says. "That’s what I’d use for trade bait for making deals without diluting my collection. I was able to use those in trade for other things, or by selling them outright and using that money to flush it back into the hobby."

Married life and children changed the frequency with which Cleveland would jump at a moment’s notice to follow a lead to the far corners of the earth, though he still attends a handful of auctions and poster shows annually. Despite being married for 21 years, Cleveland says that his passion for film posters has not rubbed off on his wife. But that doesn’t surprise him. "The acquisition of these things is like giving birth, it’s never pretty," he explains. "Even the auctions … they sound exciting, but the hard reality is, you have to sit there for four hours to wait on the stuff that you’re interested in. Your ass hurts, the guy behind you is kicking your chair, and you’re bored stiff. Unless you love the stuff, it’s painful."

Cleveland can tick off the remaining posters that he’s searching for almost on one hand, and he says that it was the hunt that always provided the greatest thrill. "A lot of the fun is in the acquisition of this stuff. I get a total high on the acquisition. It’s about the process and the excitement of hunting this stuff down that’s so rewarding. In the early decades, I was stopping at every single antique store along the way from Boston up to Maine on Route 1. Those were the major hunts."

These days, Cleveland’s collection is 20,000 posters strong, and he continues to display a small portion of it in his Chicago-area home, rotating through his favorites and hanging them in custom-made Lucite frames. But the rest, he hopes, might someday see the inside of a museum gallery. "There are only so many master paintings that you can see," he says. "These [posters] are a way that museums can bring fresh material to people—material that people don’t even know exists."

"They’re one of the few indigenous art forms that are underappreciated in this country and around the world," Cleveland continues, speaking of the classic posters that he and his peers collect. "They’re examples of very influential cultural pieces within our history, and they should have a much bigger prominence than they do."