Cigar Aficionado

The 100-year-old farmhouse is set back in a hollow near Franklin, Tennessee, about 15 miles south of Nashville—up a long driveway from the nearest road. No gates—just a sign as you enter notifying you that this is private property.

It’s actually the guesthouse, just down the hill from the big house where country-music star Brad Paisley and his wife, actress Kimberly Williams-Paisley, live with their two young sons (Huck, 5, and Jasper, 2). There are horses grazing in the pasture beyond a fence; on another part of the property, deer wander.

In fact, the Paisleys lived in this four-bedroom guesthouse (the original structure has been expanded significantly) while they were building their main residence a few years ago. Now, for Paisley, this house is Creativity Central—the place where it all happens.

“We wrote every song on my last two records in this room,” he says, sitting in a living room that features a drum kit and piano (and a scuffed solid-body red Fender guitar) to go with the nicely appointed yet thoroughly homey furnishings. Tall, lean and broad-shouldered, Paisley is dressed casually: long-sleeved T-shirt, navy-blue pants from a tracksuit, sneakers and a baseball cap with a logo for Hendrick Motorsports.

“We’d have six people writing at one time. There were times when I had them writing in here while I was upstairs in the studio recording. This house has the greatest vibe for me. I don’t think I know how to write at the other house.”

As he gets ready to launch his 2012 tour—dubbed “The Virtual Reality World Tour 2012” by Paisley—on this afternoon a week before Christmas, his witty song, “Camouflage,” is still on Billboard’s Country Top 20; so is his most recent album, “This Is Country Music,” eight months after its release (including a stint in the No. 1 slot). Paisley’s music publishing company, Sea Gayle Music, was ASCAP Country Publisher of the Year for 2010.

Paisley has had 19 No. 1 songs since he released his first album, “Who Needs Pictures,” in 1999. Ten albums later (including a double-album compilation called “Hits Alive!”), his mantle (or, more accurately, his parents’ mantle) is clogged with award statuettes: from the Academy of Country Music’s Top New Artist award in 1999, to Grammy Awards for both his instrumentals and as a vocalist, to several awards as Top Male Vocalist from both the Academy of Country Music and Country Music Association. In 2010, he was named both CMA’s Entertainer of the Year and Artist of the Year at the American Country Awards.

As it happened, Paisley was the cohost (with Carrie Underwood) of the televised CMA award show the night he won Entertainer of the Year. He’s handled the hosting chores for four straight years—including writing comedy material for himself and Underwood.

“The day after the last CMA show, those women on ‘The View’ were saying, ‘Why don’t they get whoever wrote that show to write the Oscars?’ ” recalls Kendal Marcy, who, as leader of Paisley’s band, the Drama Kings, has played with him for 13 years. “In other words, professional writers don’t do as good a job as Brad did.”

And that’s not to mention the computer-animated cartoons that Paisley does himself, which play on the mammoth video screens that are part of his concert presentation. Paisley loves to draw and is also a self-taught painter; he schooled himself in the computer software that creates comic animated adventures starring cartoon versions of himself and his band as superheroes, which show behind them while they unwind an instrumental like “Time Warp” in concert.

“He asked me about cartoons—about how they do the animation on ‘South Park,’ ” recalls Scott Scovil, owner of Moo TV, which handles Paisley’s video production on tour. “I said, ‘Well, there’s software called Toon Boom, but it takes some training,’ and he says, ‘Toon Boom. Got it,’ and hangs up. And a few days later, I show up at rehearsal and he says, ‘Hey, you’ve got to see what I did. I made this little cartoon about me and the band.’ And he’d made an animated four-minute cartoon—except it went from one screen to the other, so he’d actually made TWO four-minute cartoons that fit together.”

“The first time I tried a cartoon, it looked bad, but it was campy and cool—and the audience just erupted,” Paisley says. “It turned the audience into a bunch of kids on Saturday morning. Since then, every tour I’ve done something new like that.”
He has his finger on every facet of the concert presentation, using rehearsals to tweak the visuals and spitball new ideas. He’s hands-on about the in-concert video—and about the band’s music videos, getting intricately involved with the conception, execution and editing.

“I like the process of controlling what’s going on behind me,” Paisley says. “Editing is a big part of the touring process. Some of the clips we show I might have edited myself on Final Cut Pro. With the music videos, I tend to go in with the editors and have a big hand in what we end up with. It’s as much of a creative outlet as anything else. I like it when somebody shows up for one of my shows and sees something new. You want them to be blown away because there’s so much more to the show than they expected.”

“People would be surprised at what an amazing editor this dude is,” says Bill Simmons, Paisley’s manager. “There have been two or three videos where I thought, ‘This is awful,’ until Brad got into the editing room. He’s a true renaissance man.”

Ask Paisley to describe himself, however, and he says, “I think of myself as a guitar player, first and foremost. My job description is songwriter. That’s why I’m hired to do what I do. I happen to sing—and I get to play guitar. But I was hired by the fans to write and sing those songs.

“I’ve had 25 or 30 singles. You take those and replace them with another 30 songs and I’m a failure. So it’s not about me—being me isn’t my job. My job is to write songs. If you start thinking that the people are there to see you wear your jeans tight onstage, well, they’re not there to see that. If I hadn’t had a hit with my records, I’d still be a songwriter and a guitar player. I think I could have made a living playing, whether it was in the studio or in someone else’s band.”

In his best-selling memoir, Diary of a Player: How My Musical Heroes Made a Guitar Man Out of Me (Howard Books/Simon & Schuster, 2011), Paisley reminisces affectionately about his first guitar—a Sears Silvertone, with the amplifier built into the case, given to him for Christmas 1980 by his grandfather, whose instrument it had been. That guitar currently sits next to one of his signature paisley-decorated electric models in a display case in the Country Music Hall of Fame in Nashville.

“Truth be told, this may not have been the best first guitar choice for an eight-year-old kid,” Paisley writes. “At the time, that made no difference whatsoever—I quickly plugged it in and tried my little hands at playing it, thrilled to make some kind of noise of my own…From my perspective, a guitar is the most life-changing machine there is and offers the greatest return on investment you can get.”

Paisley grew up in Glen Dale, West Virginia, near Wheeling, where his father worked for the state’s Department of Transportation and his mother was a teacher. After getting that first guitar, he began taking lessons—and wrote his first song when he was 12, “Born on Christmas Day” (which was included on his 2006 album, “Brad Paisley Christmas,” in a mix that included samples from a recording made when he was 13).

The young Brad began performing at local Rotary lunches and church functions, leading a band, Brad Paisley and the C-Notes, that included his guitar teacher, Hank Goddard, and several other players—all his grandfather’s age. The host of a Wheeling radio show, “Jamboree USA,” heard him play and invited him to play on the program—and he became a regular fixture on the regional broadcast, playing with the big names in country music on a weekly basis as a teen.

After high school, Paisley followed his parents’ wishes and went to college: first at local West Liberty University, then at Belmont University in Nashville—mecca to the aspiring country-music artist—where he made connections that became the roots of his career. He met fellow songwriters Frank Rogers, Kelley Lovelace and Chris DuBois, who have remained creative partners, with Rogers producing his albums. They would meet after work everyday, spend all night writing songs and, surreptitiously, work in the college’s recording studio.

“We wrote like it was a free buffet,” Paisley recalls. “Some of us had day jobs—so they’d come to the apartment at six when they got off and we would write songs from six at night until three or four in the morning. None of us had anything better to do—we were all hopelessly single.

“It would be, ‘What idea do you have today?’ and we’d have three ideas for songs. So we’d start one, get about halfway through, then start on another, get halfway through that before we went back to the first one—and there was still a third one we hadn’t started yet. Sometimes we spent all night in the studio because it was easier not to stop. I can’t believe I got by on that little sleep.”

Guitars continue to define his life. He lost a chunk of his collection in a 2010 flood that submerged Nashville, destroying all of his touring instruments and gear three weeks before the start of a tour. He still got the tour off the ground on time, replacing the nine or ten guitars he regularly used in concert.

His collection includes about 75 guitars; one room of the guesthouse has a dozen instruments hanging on the walls, including one with the neck attached to a body carved in the shape of a jumping fish (reflecting both Paisley’s ion for fishing and the success of his hit “I’m Gonna Miss Her [The Fishing Song]”). Two treasured gifts hang near each other: One is inscribed by the late Buck Owens, who gave it to him; the other is a guitar given to him after the flood by Roy Clark. Nearby hangs a commemorative guitar, given to new inductees to the Grand Ole Opry (Paisley was inducted in 2001).

“I think I’ve got an acoustic guitar in every room in my house,” Paisley allows. “If I walk into a room and there’s nothing to be done, I’ll pick one up and just play. It’s like a crazy appendage. They’re all a little bit different and each one brings something different out of you.”

Many of his guitars are made by Bill Crook of Crook Custom Guitars, but Paisley also owns Fender Stratocasters, and Gibson acoustics: “I’m not monogamous,” he says with a smile.

Paisley—who has songs in several editions of the “Guitar Hero” video game—has developed a reputation as one of country music’s most inventive and nimble-fingered guitarists, someone who fills each nook and cranny of every tune with tasty guitar fills and frills: “One of the things you can bet  on with any new song we do is that Brad will want a lot of guitar solos,” says Marcy, who plays keyboards, banjo and mandolin in the band.

Paisley has a distinctively twangy guitar tone, country filtered through Duane Eddy and Dick Dale: “But when he plays with other players, he’ll gravitate to their zone,” Marcy says. “He starts to cop what they’re doing. He has the ability to clone their sound.”

Adds Paisley’s drummer Ben Sesar, “He’s kind of a chameleon. And he’s the kind of player who will never have a peak as to how good he can be—it’s just steadily up. The older he gets, the more rich and complex his playing gets.”

Paisley has his own guitar heroes, many of whom he’s played with. He won a pair of Grammy Awards for best country instrumental, including for “Cluster Pluck,” for which he gathered such noted pickers as James Burton (who backed both Elvis Presley and Ricky Nelson), Vince Gill, John Jorgenson, Steve Wariner and Albert Lee to trade licks. He’s played onstage with Buck Owens and Roy Clark, but also with Brian Setzer, and recorded a duet of “Let the Good Times Roll” with blues legend B.B. King for his album, “Play.”

Paisley is modest about his own abilities. While he loves to cut loose with an instrumental in concert, “I think if I said, ‘I won’t be singing tonight,’ we would have a problem. They want to hear the songs when I play a concert.”

There are still players with whom Paisley would love to sit in, a list that starts with guitar god Eric Clapton.

“I’ve even said that on ‘The Tonight Show,’ ” Paisley says with a smile. “In fact, I say it in every interview I give. I guess he’s avoiding me.”

Eddie Van Halen is also at the top of his wish-list: “And I’d really love to play with the Eagles—just to get up and play at the end of the night, those double-guitar parts on ‘Hotel California.’ I know all those guys, but I’ve never been to an Eagles concert.”

Paisley gets into shape for a tour with an exercise regimen of running and weights (and stretching, to fend off back problems that have occasionally bothered him). He doesn’t drink alcohol—never has, though, as he says, “I’ve tasted beer a couple of times”—or indulge in drugs (“Except antibiotics,” he notes).

His sole vice? A love of fine tobacco. Cigars, he says, have become not just a favored way to celebrate a good concert—they’re a ion and a source of relaxation, thanks to the teachings of Sesar, his long-time drummer, and Marcy, his bandleader.

Sesar had quit smoking cigarettes but had taken up cigars, which struck Paisley as odd: “But he told me that smoking cigars is nothing like smoking cigarettes,” Paisley recalls. “Cigarettes are a habit—but cigars are an event. Cigars are something that require focus; they’re not something you lean on. They’re something you consciously decide to do.”

His first cigar? A Cuban Montecristo he bought while on tour in Canada: “My drummer told me to sip the smoke, like water through a straw. He said to take little puffs, so it didn’t get in my lungs. He told me, ‘You’ve got to taste the smoke on your tongue, let it roll around and then blow it out completely.’ He also told me the taste would change throughout. I had a good teacher.”

Now it’s become something of a ritual: After a particularly satisfying concert, after the crowd has left, Paisley, Sesar and Marcy will wander up into seats in the upper reaches of the arena they’ve just played, light a cigar and watch the road crew tear down the stage: “It really puts a cap on the day,” Paisley says.

“Brad is very sophisticated in his taste,” Marcy says. Adds Sesar, “He can peel back the flavors with the best of them. He could be one of those guys who rates the cigars for Cigar Aficionado. We’re all cigar geeks, really.”

Certain post-show cigars come to mind for Paisley: after a rollicking set in front of a sold-out crowd at Gillette Stadium in Foxborough,  Massachusetts, in August 2010, or following a June 2011 concert at Progressive Field in Cleveland.

“It had been threatening rain all day in Cleveland but we did the show without it actually raining,” Paisley recalls. “When the show was over, we went and sat in the Cleveland Indians’ dugout while they tore down the stage and lit our cigars. And it started to pour. That’s pretty fun—we’d played really well and just got the cigars lit. And we just sat and watched it rain and talked about the show.”

Observes Marcy, “Having those cigars after the show—that’s like our way of spiking the football. There’s always a new tour, always a new song to learn, always a new horizon. But we take those little moments to spike the ball—to give thanks, celebrate, feel proud and then move on.”

“We don’t just casually have a cigar,” Sesar adds. “It’s not taken for granted. It’s always reflective.”

Paisley seconds that notion: “When I’m smoking a cigar, I don’t want to be doing anything else—I’ve got to sit and think. There’s something that feels almost Native American about it. That’s where it comes from, right? It’s our peace pipe; we use it to sit and think about the future and what we’ve just done. It’s kind of a Zen feeling. I look at it like dessert.”

He thought about it enough that he wrote “The Cigar Song,” which appeared on his “Mud on the Tires” album. The tune is a humorous tale of guy who buys himself a box of expensive Cubans and insures them against fire and theft. He smokes them all “one by one,” then submits a claim to his insurance agent: “With a straight face I told him that through a series of small fires/They’d all gone up in flames.”

Paisley has a pair of humidors in the guesthouse and another on his tour bus. Since he’s become known as a cigar lover, concert promoters tend to lavish boxes of cigars on him in recognition of sold-out shows: “It’s kind of the go-to, easy gift. Honestly, I’ve probably got more than I need, but don’t tell anyone. You can never have too many cigars.”

When he’s touring, Paisley tends to save his cigar smoking for the end of the week, to preserve his voice: “For me, Saturday night is a good night. If I’ve got a four-day weekend where I’m playing four cities and I smoke one on Thursday, by the Sunday show I’ll be in trouble, if I don’t watch my voice and how I sing.”

He enjoys a variety of cigars, though he favors a Montecristo No. 2 or a Punch Grand Cru: “I like something complex,” he says, “something where the cigar changes throughout. I don’t like that tingly, sore-throat feeling from an overly spicy cigar. But I don’t rely on any one thing. I find CAOs are very consistent—but I’ve got these Cuban Cohibas a promoter gave me for when I’m in the mood for a big, intense experience.”

His band tend to enjoy the cigars while sipping a fine whiskey, or a glass of wine. But the nondrinking Paisley has his own favorite beverage when savoring a cigar.

“If you have a Yoo-hoo with a cigar, it’s like a s’more,” Paisley enthuses. “Anything chocolate is fantastic. A hit of chocolate takes the bite away. A chocolate milkshake with a cigar? That’s just decadent. Grape juice is good, too. Anything thick and sweet is pretty cool. I think I’d like port, if I did that.”

As he spoke, Paisley was gearing up for his 2012 tour, which kicked off in mid-January with back-to-back shows in the deep-freeze belt: Grand Rapids, Michigan; Milwaukee, Wisconsin; and St. Paul, Minnesota.

“The first time I saw the schedule, I thinking, who is the idiot in the organization that had this idea?” Paisley says. “But it’s brilliant, really. I’ve played Minnesota in the summer and the winter. Nobody in Minnesota is all that excited about wasting one minute indoors in the summer  because their summers are, like, five minutes long. But if you play St. Paul in the winter, they’re ecstatic to see you. There’s this amazing excitement level, because you gave them something else to think about other than avoiding frostbite.”

Forbes magazine ranked Paisley third among country music’s highest-paid stars in September 2011 (and No. 48 among all celebrities), estimating that he grossed $40 million between May 2010 and May 2011—which, they estimate, was double from the year before. (Paisley’s management wouldn’t comment on the figures.) That includes tour revenues, CD sales (“This Is Country Music” went gold in a month), publishing rights for his music and income from endorsement deals with Chevy and Sea Ray, among others.

But growing up in a family with two working parents, Paisley understood the value of money earned. He may have the resources of an entertainment mogul, but he says, “I don’t let the fact that I’ve made a lot of money go to my head—I wasn’t born that way.

“It’s hard to get out of the mindset of what it was like before I had anything. I still think that way. It’s funny, because it’s true whether I’m pricing a guitar pedal on eBay—and thinking that, well, I’d pay $200 but $275 seems a little pricey—or when I’m trying to decide whether to pull the trigger on five lasers instead of four for the live show, which cost thousands a day. “I really try to that it’s all finite. No matter how much you’ve got, there’s not an endless supply of good fortune.”

He recalls contests he and writing partner Kelly Lovelace would have in college, where they’d go grocery shopping at the local Kroger market to see who could spend the least on a week’s supply of food: “I could get a week’s worth for $15 to $17,” Paisley says with a laugh. “Kraft macaroni and cheese was 59 cents; a package of Ramen noodles was 99 cents. Milk, cereal, eggs—what else did I need?”

His one indulgence is the private jet he charters when he’s on the road, an expense that’s built into the budget for the tour. Even then, he doesn’t use it daily: He’ll fly to the first stop of a four-day concert weekend on the day of the show, ride the bus between stops, then fly home right after the last one: “It lets me spend more time with my family. Most entertainers at my level do that.”

Paisley sold more than a million concert tickets last year, placing him among the top touring acts in popular music. And he does it by appealing primarily to his base of country-music fans. While he may be a monster guitar player and one of the biggest acts on the country scene, Paisley has yet to cross over to the rest of the music audience the way that, say, teen sensation Taylor Swift has.

That’s the challenge he faces at this point: Having hit a pinnacle in his field, can Brad Paisley reach the mass-market audience? Certainly, Paisley has achieved mainstream benchmarks, playing on “Good Morning America,” “The Tonight Show” with Jay Leno and “The Late Show” with David Letterman (though he still hasn’t garnered an invitation from “Saturday Night Live”), as well as hosting those CMA awards shows. He’s cracked the market in Europe and the Far East, selling out arena shows from London to Tokyo—with Central and South America the next territory he’s prepared to conquer.

“He’s done everything there is to do in country,” Rob Beckham, his agent, says. “He’s in the forefront with country, and we’re expanding to the rest of the world. His celebrity is so big—and it’s getting bigger by the day. But I don’t know if he’ll ever cross over to the pop audience. The only thing that hinders him is the cowboy hat; it’s such a trademark, but in the mainstream pop world, a lot of people don’t think the hat is cool. Still, when we were playing Europe, he sold out a show in London just by putting out a couple of tweets on Twitter. And we sold about 500 of those cowboy hats at the concert.”

Bill Simmons, his manager, believes that Paisley doesn’t need to court the mainstream audience because it will find its way to him. Rather than dilute his brand by making more pop-sounding tunes, Paisley is moving in other directions: contributing music to movies (he wrote songs for the soundtracks of both Cars and Cars 2), producing (he was a producer for a TV pilot that didn’t get picked up), perhaps even as an actor: “As for the cowboy hat, well, the lines of musical genres are always blurring,” Simmons says. “I don’t know that he’s consciously trying to cross over.”

Indeed, Paisley offered something of a manifesto of his beliefs in the title tune of his most recent album, “This Is Country Music.” The song explains that, while some of the topics country music deals with—everything from cancer and Jesus to “tractors, trucks, little towns and mama”—may not seem hip to the cognoscenti, “This is real, this is your life in a song/Yeah, this is country music.”

Yes, Paisley its, the song indicates a small chip on his shoulder about the genre: “There are still misconceptions—I’m asked all the time what makes something ‘country’,” he says. “My conclusion is that we don’t shy away from the specifics of life. We don’t find glossy, poetic ways around things. These are songs that deal with divorce, religion, patriotism. If you’ve got a heartache, you tell why. And really, there aren’t many pop songs that deal with anything other than heartache.”

Paisley also isn’t afraid to infuse his songs with humor. Tunes like “I’m Gonna Miss Her,” “Online,” “Ticks” and “Celebrity” are like extended but sly punchlines, jokes within jokes, set to juicy guitar licks and well-wrought production. A song like “The Pants” (“It’s not who wears the pants/It’s who wears the skirt”) is smart and witty, falling squarely within a venerable country tradition of telling it exactly like it is.

“I envy writers who can create imagery that’s less nail-on-the-head-type writing,” he says. “I’d love to be able to write something along the lines of what Bono would write, where you’re not necessarily sure what happened to the person who’s singing, even though you know what they’re feeling. A common complaint from the record company about a new song of mine is, ‘I don’t know what you mean.’ In pop, that doesn’t even enter the thought process. I don’t know what most pop songs mean. I listen to pop stations all the time—and I don’t want to turn on a pop station and hear a song about divorce or losing a job. That’s our real estate. When I listen to pop music, I want to hear metaphors, songs about loss told through imagery of planets hurling away into space. I love the Foo Fighters—but when I hear Dave Grohl singing, ‘Learning to walk again,’ I don’t want to hear the specifics of what Dave’s thinking.”

That doesn’t mean that Paisley wouldn’t like to reach that audience; he just wants to do it on his own . He saw Coldplay at Lollapalooza in Chicago in August 2011 (“That was pretty wild”) and contemplates getting the chance to show what he can do for an audience not primed for country music.

“I’d love to play at something like Lollapalooza,” he says. “I’d be lying if I said I didn’t want to walk out and impress a crowd of people not normally in earshot of my music. It would have to be unexpected and unannounced. That’s where the guitar would be a real vehicle for me. As much as I love country, I’m a guitar player who was influenced as much by Eric Clapton and Eddie Van Halen as by Don Rich.”

Paisley’s tour will take him into the fall, when he’ll turn 40: “It’s not that big a deal,” he says. “Forty is the new 15.” When the tour is finished, he’ll focus on his next album—and he feels as though the next one affords him a unique opportunity.

“You’re catching me at an interesting time,” he says. “I feel like I have to do something different but I don’t know what it is. I feel I can improve in a way I couldn’t have before. How do you satisfy yourself completely with what you have created? How do you dig down deep and find that? Because it takes digging. And you don’t stop until you’re pretty happy. It’s not going to be easy. There were prolific periods where I felt I could do no wrong but I don’t think I’m there now.

“I’m itching to do something that makes me stick my chest out as I hand you the CD. I do think it will be harder. But I want one this time where I’m going insane because it’s not out yet because I’m that excited about it. I’m not sure what form it will take. A clean slate is a good place to be. I don’t want to rehash what I’ve done before. Of course, every time I’ve tried to be completely different, it sounds like me in the end. We’ll see. I guess right now I’ve got one foot on the boat and one foot on the dock.”

Contributing editor Marshall Fine writes about movies and entertainment on his website, www.hollywoodandfine.com.