At age 53, Maynard James Keenan may be contemplating his mortality — or immortality. “[Music's] a wonderful legacy, but that legacy's all about you,” he says, sitting in a sleek North Hollywood recording studio one recent morning. Up close, the famously enigmatic Tool frontman and maverick winemaker is a trim, tidy man with the unhurried air of someone seldom interrupted. “This connection with the winery, it ends up being about us; it ends up being about that place. That outlives and outlasts any particular individual.”

One of Keenan's latest projects has given him cause for reflection: his authorized biography, written with longtime friend Sarah Jensen. A Perfect Union of Contrary Things, which he describes as partly “a map for my kids,” was released in October to favorable reviews.

Now, 25 years after Tool's debut release, the furiously productive Keenan is attaining another bio-worthy landmark by finally headlining the iconic Hollywood Bowl on May 7. Only not with Tool. Instead, he'll be fronting A Perfect Circle, the more melodic and accessible group he created with former Tool guitar tech Billy Howerdel in 1999. It'll be a fitting hometown finale for the band's first U.S. tour in six years.

A so-called side project playing a 17,500-capacity amphitheater is all the more remarkable considering that APC has released only two original albums, Mer de Noms and Thirteenth Step, both back in the early 2000s. But the March announcement that the band had signed a recording deal with BMG and begun work on a new album fanned long-lingering interest in their ethereal yet energized expressions.

Keenan confirms that Howerdel has been sending him instrumental demos, but deadpans, “I'm a prick when it comes to that. … I'll strip it down to the click track and just the bass and [say] let me play, vocally, with just that piece and see if we can build it up from nothing.”

Raised in Ohio and Michigan, Keenan's childhood ambitions alternated between “soldier” and “artist.” He achieved both, serving in the U.S. Army in the early 1980s. Arriving in L.A. in 1989, he worked in pet-store design and set decoration until his prog-metal foursome Tool turned pro a couple of years later.

Keenan's unlikely marriage of militaristic discipline and irreverent creativity has manifested on 10 studio albums, with Tool, A Perfect Circle and parody act–turned–serious project Puscifer. More than half of these records — that is, all of Tool's and APC's — went platinum and, with their dramatic, ultra-dynamic arrangements and dark lyrical themes, have been widely hailed as major influences on contemporary hard rock.

“Now Billy's in a different place, I'm in a different place — it's time to see how we can challenge each other to draw outside the box that we kind of put ourselves in,” Keenan says. “He's done his own work outside of A Perfect Circle; he's done some producing, some scoring, [has] his own band, Ashes Divide. So he's been out there and he's actually had to be on my end of it … [so] it's a much more stable, solid relationship now.”

A Perfect Circle is the most radio-friendly and romantic of Keenan's musical projects, with alternately twinkling and chugging guitars, stark beats and ominous bass lines lurking somewhere between inquisitive heavy rock and Disintegration-era Cure.

Like his other bands, APC is L.A.-based. But Keenan himself moved to tiny Jerome, Arizona, in 1995, carving out his own winery, Caduceus Cellars, in an area not previously known for winemaking. Today, he juggles the life of a contemplative rock shaman with literally dirtying his hands (and operating the forklift) tending the small-production operation. Indeed, the grape harvest lately takes priority over lucrative concert tours. “I challenge you to find a show date between Aug. 1 and Oct. 15 over the last 10, 12 years,” Keenan says.

Yet he has long reveled in obligations and responsibilities that others might find frustrating — in solving the puzzle of self-expressing within fixed parameters for extended periods (such as tours, both military and musical).

“I think it's liberating,” he says. “It helps my other fellow artists understand that there's a rhythm to things. … There's a big 'click track' happening that you're a part of, whether you like it or not.”

Keenan views his vineyard as another thread in his creative conversation, as eloquent as lyrics or melody. And his winemaking philosophy may be a metaphor for his uncluttered, meticulous approach to making music.

“You're expressing a place … if [winemakers] get out of the way and they don't cut corners,” he explains. “As soon as you get greedy — you crop extra fruit, you do all kinds of manipulation in the cellar — it's no longer from that place. It's just a product now.”

“I’m a firm believer in the beauty of simplicity.” —Maynard James Keenan

As early as 1987, in a rambling manifesto accompanying demo tapes by his first band, C.A.D., Keenan lamented, “No longer do we experience the harmonious interaction between each other and our environment.” He regards such relationships as having been largely lost during the epic shift from family farming to industrialization during the World Wars and, between these, the social turmoil of Prohibition (“it gave us all amnesia”) and the Great Depression.

“We switched to 9-to-5 factory work … [and] now the kid goes to school to be raised by some stranger,” he says. “Food comes in a can, food comes frozen — all these things that remove your connection with that core family experience. … You don't think of anything that came before and all the work that went in.”

Winemaking allows Keenan to collaborate not only with other people but also with the Earth's topography, soil and seasons. “You can find [similar] connection in the songs … you can find your own, as it were, terroir,” he says.

A Perfect Union of Contrary Things is a coherent and detailed account that devotes considerable space to Keenan's prefame journey (he was 27 before Tool released a record). “Only part of my story is told — the rest of it dies with me,” he says. “I needed to at least get some of that stuff written down, so that [my children] had a memory.”

Recognizing the often unseen roots of very apparent fruits — be it a rich rock star's backstory or the process behind a bottle of wine — is a recurring theme in all that Keenan does. A Perfect Union deftly relates his leadership and self-discipline as a teenage wrestler, cross-country runner and West Point cadet with his uncompromising yet broadly resonating creative existence since. But, as he and Howerdel teeter back and forth toward further A Perfect Circle recordings, there's also sheer artistry at work.

“It's like scraps of paper all over the floor with different ideas,” Keenan says. “I'm a firm believer in the beauty of simplicity. Like Italian cooking … you get it wrong, it's a tragic mess; but when you get it right, it sings.”

With a lineup unchanged from their last performances, at Keenan's two-night, 50th-birthday bash at the Greek Theatre three years ago — completed by drummer Jeff Friedl, ex-Puscifer bassist Matt McJunkins and former Smashing Pumpkins guitarist James Iha — A Perfect Circle swiftly sold out much of their current, monthlong trek. Topping the bill at the Bowl will ice the comeback cake, but Keenan will be leaving any reverence for the storied venue in his dressing room.

“I'm kind of a rain man, so I just need to be in my space,” he says. “When it actually comes down to the show … it can be in your mom's house.”

A PERFECT CIRCLE | Hollywood Bowl, 2301 Highland Ave., Hollywood | Sun., May 7, 7 p.m. | $32.50-$344 |

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