Brandon Butler has been a musician for most of his adult life. In the early and mid-’90s the 35-year-old Kansas City, Mo., native made records with scrappy indie-rock bands like Boys Life and Farewell Bend. Once he moved to D.C., he wrote expansive, spaced-out country ballads as the guitarist and lead singer of Canyon. He recalls getting a royalty check exactly once. “Slowdime paid me one time,” referring to the now-defunct D.C. label that released Farewell Bend’s 1998 album, In Passing. “It was $600. Not bad. We sold 1,800 records in one month, 200 records next month, and then no other records ever. I’m still living with 500 Farewell Bend albums.”

Tours also left Butler relatively cash-strapped. Even after Canyon spent the fall of 2004 as both opening act and backing band for alt-country bigwig Jay Farrar, Butler came home with about $400 in his pocket. “[Being a musician] has always cost me money,” he says. “It’s always been a financial burden, fucked up every relationship I’ve ever had. I drank too much, stayed up too late, I lived out of vans and Taco Bells.” These days he works as a carpenter, playing music on the side.

If you’re a musician and you can’t sell records or concert tickets, there’s not much left for you to sell. That’s traditionally the moment where your dreams end and straight jobs begin. That is, unless your music is capable of selling something else entirely: a car, a cup of coffee, broadband Internet. Over the past 15 years the people who choose music for advertisements, television shows, video games, and films have become much more willing to license the work of lesser-known artists. In turn, labels and musicians, facing the apocalyptic realities of illegal music downloading, have softened up on selling out. Some of them have even made some decent money.

Butler, for one, sure wouldn’t mind. His music career has been full of missed opportunities and withering fortunes. It’s the kind of story that could drive you to drink. It could drive you to drink beer. A couple of beers, even. And if you’re a brewer that hopes to capitalize on that—to maybe use one of Butler’s songs in a TV ad—Butler and his label, Gypsy Eyes, might like to hear from you.

No matter what he’s discussing—distribution woes, declining sales, the rapidly accelerating cycles of the Mayan calendar—Kalani Tifford always sounds relaxed. His affable surfer drawl suggests that the offices of Gypsy Eyes, the record label that he manages, is headquartered not in Glover Park but inside of a Jimmy Buffet song.

Tifford, 35, founded Gypsy Eyes in 2006 with his friends Josh Read and Nick Pimentel. Tifford already had plenty of experience in the music business, having spent most of his professional life helping to run ESL Music, the label owned by local downtempo gurus Thievery Corporation. Tifford liked Thievery Corporation’s smooth and sitar-heavy elevator disco, but classic-rock artists like Jimi Hendrix and the Grateful Dead were a little closer to his heart. He saw a lot of potential in the rootsier music that his singer-songwriter friends like Mark Charles (aka Vandaveer) and Brandon Butler were playing, as well as local bands like Shortstack and Read’s group, Revival. They played sad and heavy songs, and they were part of a local music community that had spent years trying hard and not getting anywhere.

Gypsy Eyes was launched in the hope of validating all that hard work. “The point is to give people a career doing music—doing what they love,” Tifford says. “I believe that we’re on that path, and it’s only a matter of time.”

Kalani Tifford(Photograph by Darrow Montgomery)

So far that path has had a few potholes. Gypsy Eyes has put out eight releases, but sales have been lackluster: According to Nielsen SoundScan, which tracks sales from digital and brick-and-mortar retailers, Vandaveer’s 2007 album, Grace & Speed, sold approximately 700 copies, while most of the label’s releases have sold in the low hundreds. It hasn’t helped that the music industry is in a recession that predates the broader downturn or that some of the magazines sympathetic to the label’s music, such as Harp and No Depression, have folded or retooled into more modest online entities. “It was a stupid idea,” Tifford says jokingly, then quickly rescinds the statement. “It wasn’t a stupid idea.…But it has certainly been very difficult.”

Worse, Gypsy Eyes couldn’t get the word out on the road: Due to jobs and family commitments, the majority of the label’s signees could rarely tour. “I didn’t anticipate the touring being such a big part of it,” says Tifford. “And without huge sales numbers you can’t get a good booker. For these guys to go out on the road—they’re booking shows themselves and everybody’s got bills. Everybody’s older.”

But from the start, Tifford figured he could compensate for a road-averse roster by using his old ESL contacts to court one of Thievery Corporation’s major income sources: licensing.

In Tifford’s mind, licensing—selling music for use in advertisements, television shows, films, video games, and more—had dual benefits. One was financial gain: When advertising firms license a song, they generally pay princely sums. Depending on the deal and type of use, an artist can make anywhere from $500 to $50,000, according to Garo Kuymcuovic of Los Angeles-based Rooftop Promotion, a firm that helps musicians and labels land licensing deals. Even the lowest compensation would help the label recover the costs of pressing and promoting records, and licensing had promotional value too. If, say, Brandon Butler’s song “Fire and the Wheel,” were featured during the weepy climax of an episode of Gilmore Girls, it might send zillions of tear-streaked teens to the iTunes store.

Such efforts have become standard practice at many indie labels. “We actively pursue it,” says Jeff Tafolla, who works for the Omaha, Neb., label Saddle Creek, home to bands like Bright Eyes and Tokyo Police Club. One part of his job is to regularly pitch the label’s artists to music supervisors. “Overall, it’s been a growing part of our business in a time when record sales are down. It can make the biggest difference for a smaller artist. We have some records that would have never recouped without licensing, but they are now making royalties from every sale.”

Brian Lowit, owner of Arlington-based label Lovitt Records, doesn’t actively court licensing money, but over the past couple of years he’s been approached a number of times by fans turned benefactors, usually out of the blue. “There are people that come to us and say, ‘Hey we really like this band, we want to use one of their songs on X video game, skate video, or MTV Real World episode,’” he says. “I ask the band if they’re interested and find out how much it pays.”

Brandon Butler (Photograph by Darrow Montgomery)

Some artists have reservations. For instance, D.C. noise-rock trio Navies in 2005 asked Lovitt to not include its music on a label compilation CD that was being sold exclusively at Hot Topic stores. But age tends to make some musicians more open to such deals. John Davis, who’s played in Q and Not U and Georgie James, knows when he began to change his attitude about licensing. “It was when I stopped living in group houses and got married—when things changed and everything stopped being about me,” he says. “When all I had to do was pay my rent, it was very easy to be dogmatic. But if I want to be a musician—which I do, more than anything in the world—there are certain ways to make money.”

The stigma doesn’t weigh too heavily on Brandon Butler either. “The only thing that would be kind of a bummer would be [a licensing deal with] big tobacco. I wouldn’t want their money,” he says. “The short answer is I don’t care.”

Through the contacts he assembled working for ESL, Tifford scored Gypsy Eyes a publishing deal with Bug Music and also took up with a few independent promotional firms like Rooftop Promotion in the hope of marrying the label’s music to other, potentially more profitable, media. These firms don’t collect a regular fee but instead draw a percentage of publishing and licensing revenue. They regularly e-mail Tifford advertising-firm requests, which usually include a few vague adjectives about what kind of music is being sought, like “fast” or “intelligent.” Tifford sends back songs that he deems appropriate. Then he waits.

By last July, the eagle hadn’t landed. There were a few close calls: A Brandon Butler song was accepted for a national marketing campaign, but the deal fell through. A song by Jon Bustine was considered for an episode of the TV show Eli Stone, but that deal also fell apart. “We were in the show and then there was the writers’ strike,” says Tifford. “The budget got cut, and then they used stock music for a hundred bucks.”

But Tifford was confident that if the label could break in once, its fortunes would improve. “You just keep going and going until you get one,” he maintains. “One iTunes commercial, and you’re selling 15,000 records. There are certain key things that you get, and then everything falls into place.”

Whatever those key things are, Fort Knox Five seems to have a better grasp of them. The D.C. based production team—which releases beat-driven, vibrant party music on its own Fort Knox Recordings label—seems to be able to take those adjectives and spin them into actual currency.

Fort Knox member Jon Hovarth, 33, who used to manage a gas station at 22nd and P Streets NW, is now enjoying an existence entirely opposite to Brandon Butler’s. “I would say I’ve been living 100 percent off of DJing and music probably for about four years now,” says Hovarth. “I basically bought my apartment and took the leap of faith.”

Hovarth can recall several checks arriving in his mailbox just in time to pay the bills. “The money comes in from all types of little different places,” he says. “Suddenly a check shows up from [performing-rights organization] BMI. I’m starting to see a $300 check here or a $1,000 check there…little checks out of the blue that you don’t count on.”

The biggest checks generally come from licensing deals. “That’s where we make the majority of our living,” he explains. Fort Knox Five doesn’t sell many records through traditional outlets. (Nielsen SoundScan reports that its most recent record, Radio Free DC, has sold only 300 copies—not great for an act that’s DJ’d on a Gwen Stefani tour.) “There’s also digital sales, and we make a little bit of money on vinyl, but it’s more of a promotional tool,” says Hovarth. “Basically, we try to go full-forward with the licensing thing. We’ve done really well with video games—we work closely with EA Sports. [The group’s work has been featured in Tiger Woods PGA Tour 07, NBA Street Homecourt, and FaceBreaker.] It’s not huge money but a pretty steady flow. We send them anything we do, as soon as we have it mastered.” They’ve also done promotional gigs for Monster Beverage Co. in Canada (Hovarth says he’s only tasted it once), been on the soundtrack to the snowboarding documentary Let It Ride: The Craig Kelly Story, and a Kia commercial in South Korea.

Ironically, these licenses are largely obtained through the same channels that defy Gypsy Eyes. Fort Knox Recordings employs Tifford as its manager, and its promotional resources—Bug Music, Rooftop Promotion—are almost identical. So why isn’t Brandon Butler wearing a Carhartt jacket spun from strands of golden thread and spinning donuts in the monster truck that appears on the cover of his solo record, Lucky Thumbs?

Hovarth thinks it has to do with what he calls “sync-friendliness”—the ease with which music can be seamlessly connected to a moving image. “Rock is not necessarily the easiest to sync up to video,” he says. “That’s what a lot of these music supervisors are into. Any kind of music that’s got an electronic beat could be sync-friendly. Thievery [Corporation], Nicodemus, Thunderball, Fort Knox—that kind of music is the type of stuff that sits well in video game and TV placement.”

Fort Knox Five doesn’t specifically write songs with sync-friendliness in mind. But once a song is finished Horvath and his bandmates determine whether or not it contains any potentially sync-friendly elements. “One time when we were doing [a remix of] this [Afrika] Bambaataa song, this guy from Tommy Boy was like, ‘You should make a song about cell phones, it’s a multimillion biz in Asia. You make a song that mentions cell phones and they’ll give you a big endorsement,’” Hovarth says. “We were like, ‘What are you talking about?’ That’s not what we do. Instead you say, ‘I’m gonna get down and make a song,’ you make it, and then you’re like, ‘This could be a dope commercial!’”

“Afterwards you start brainstorming on that for your own good,” Hovarth adds. For example? “We have this song ‘The Party Pushers.’ In it, Mustafa [Akbar, the vocalist] is going ‘Fire it up! Fire it up!’ That could be in a Pizza Hut commercial.”

There aren’t a whole lot of Pizza Hut–worthy snippets on Lucky Thumbs, or Revival’s Horses of War, or Child BalladsCheekbone Hollows, or any other record that Gypsy Eyes has put out in the last two years. The Apes’ Ghost Games—a prog-rock record with a hyperactive sensibility that’s a clear outlier in the catalog—might be the roster’s best chance to accompany a stuffed crust.

But Tifford recently claimed a few victories. By September, after countless adjective e-mails and the pondering of said adjectives, Gypsy Eyes had managed a few licensing deals.

“We got a Cheekbone Hollows track into this movie, Assassination of a High School President,” says Tifford. “We also got Vandaveer on a Ford podcast, one of their marketing podcasts. They licensed the track for that.” How’s the money? “Um, it’s decent. It’s not a tremendous

amount of money, but [it’s] money nonetheless. I think that one put us just about even.”

And once they get even, in theory at least, everybody gets paid. Tifford explains that after expenses for the production and promotion of the record have been recouped, Gypsy Eyes splits everything with the artist. But so far there isn’t much to split. “Nobody has recouped,” says Tifford. “It’s horrible.”

Tifford will occasionally sound as if he’s being driven toward full-on madness by music supervisors. Once when we spoke about the process, his normally unflappable demeanor began to flap a bit. “It’s all a matter of…it’s the most,” Tifford says, then trails off in aggravation for a moment. “What is the word? It’s not ‘abstract’…it’s a very random event.” He’s come to think that the choices that music supervisors make are rarely based on the music itself. “There’s all of these other factors. Have I eaten today? What mood am I in? Am I pissed at my girlfriend or wife? It’s just really random. There are so many angles.”

Rooftop Promotion’s Garo Kuymcuovic mainly blames the lyrics. “It’s very hard to get a Gypsy Eyes Records song on an advertisement, [more so] than a Thievery Corporation song. Most of the time it’s a singer-songwriter. You have lyrics carrying the entire song—so you have to be lyrically toned to the commercial you’re doing. It’s hard to get the lyrical content to the advertisement.”

But for Tifford, the lyrics are the most important part of Gypsy Eyes’ music. “That stuff is beautiful to listen to,” he says, referring to electronic music. “But are they songs of revolution? What’s the point of it? Not to be ostentatious or anything.”

So he’s not inclined to start cravenly courting sync-friendly artists for Gypsy Eyes, even if it hurts his bottom line—if tales of broken hearts, toil, and trouble can’t sell a car, so be it. “With Gypsy Eyes it’s stories, poems, the hardships of life,” says Tifford. “Fort Knox is a fun party album. You put it on you’re in a good mood, forget about all this shit that’s happening in life.”

Butler appreciates the efforts of Tifford and his colleagues on his behalf, but he wasn’t really counting on a big licensing payday. “I’m like the naysayer of the whole thing,” he says. “If I had a dollar for every near-miss that I heard about, I could quit working.”

He quit checking up on sales reports and rumors a long time ago. “I don’t really care to see half of nothing,” he explains. “I know that they’re taking a bath on this shit. And they busted their ass.”

He seems acutely aware that his music isn’t going to put a slice of pizza in anybody’s mouth or a can full of taurine in a snowboarder’s hand. It turns out sad songs don’t really loan themselves to commerce. Or, possibly that the cultural trappings of an album like Lucky Thumbs just aren’t particularly glamorous. “Josh [Read] used to say that if there were a fucking dance or a look associated with Gypsy Eyes, if it were a cool thing to do, that it would blow up,” says Butler. “But with Gypsy Eyes, what can you get? A flannel shirt? A baby? A house payment?”

Due to some restructuring of the label’s distribution plan, Gypsy Eyes has slowed down its release schedule, but Tifford has tentative plans to release a new Shortstack album in 2009. He’s not entirely optimistic about the future, yet he still believes in the music that his friends are making. He’s become a little bit philosophical about the whole thing—embracing the chaos of owning a local label in a digital age when consumers are constantly bombarded by media but have no clear idea of what community or individual produced it.

“Are you familiar with the Mayan calendar?” he asks. “It has all of these different seven day/six night cycles. There’s a shift in human consciousness from a tribal culture to a universal thing. The Internet is creating that universal environment—where everything is everywhere. It’s not important where it’s from, its more important what it means. Every barrier is coming down.”