The smell of chlorine drifts in the breeze while Shooter Jennings talks about frustration and hope. The 30-year-old singer is sucking down cigarettes and nursing a Diet Coke on the poolside patio of a house he shares with his fiancée, actress Drea de Matteo.

The tangled stretch of road that leads to the couple’s front door seems as if it were drawn up by dropping a plate of spaghetti on a map of the Hollywood Hills. Jennings likes it that way. The son of country icons Waylon Jennings and Jessi Colter describes himself as a loner who cherishes his family but thrives in isolation.

“If it weren’t for Drea and the baby, and my family and my mom, I’d probably be (expletive) hanging from that tree over there,” he says. Then he laughs. The ice cubes in his glass jingle like tiny wind chimes.

Behind his aviator shades and a scraggly black beard is an artist leading a life of contradictions. He’s a singer who has embraced his late father’s legacy while continuously bucking Nashville’s definition of it.

He’s a heavily tattooed computer geek. He’s a dad who takes his 3-year-old daughter, Alabama, to dance class when he’s not writing songs about the end of the world.

His new album, “Black Ribbons,” feels in tune with the rebel spirit of his father – but certainly not the sound. Released last week, it’s a wildly ambitious, 70-minute rock opus splicing heavy-metal bombast with freedom-rock harmonies.

There are pulsing synthesizers and Allman Brothers-style guitar solos. There are songs about fame and Armageddon. There are backup vocals from Colter and skits narrated by novelist Stephen King. It feels like a country album mutated into something both exciting and unrecognizable.

“I think the whole thing is a metaphor for how hard it’s been to get my voice heard,” Jennings says of the album he’s been laboring over since 2008. “Whether it’s a success or not, at the end of the day, I know that I didn’t play by anyone’s expectations. This is the anti-expectations album.”

As the youngest child of one of country’s most mythic figures, Jennings knows all about expectations. And while Nashville has often been friendly to the progeny of its heroes – Hank Williams’ bloodline has enjoyed successes not seen by the musical children of Lennon or Dylan – he hasn’t felt the same embrace.

His 2005 solo debut, the crudely and cleverly titled “Put the ‘O’ Back in Country,” was a promising meld of rock swagger and country twang, but it failed to find a larger audience.

“When I was in the Nashville world, they let me in and they tore me to shreds,” Jennings says. “I was either too rock for (country) radio or too country for rock.”

And while he’s always felt trapped in that gray-area purgatory, he has never shied from his heritage. He still performs tribute concerts to his late father and donned a “Waylon Forever” T-shirt while performing in Washington last fall. It feels natural. But it’s not easy.

“When you go out there and say ‘I love my dad, I’m very proud of my dad,’ there’s a certain expectation that people have: To relive your dad through you,” Jennings says. “That, I think, can be your downfall if you don’t have a clear vision for what you want to do.”

Raised in Nashville, he was the only child of Waylon Jennings’ marriage to Colter. (He has siblings from Waylon Jennings’ previous marriages.) And while Jennings grew up surrounded by country music, he had no desire to be a part of it. He liked Guns N’ Roses.

At 15, he begged his father to let him attend Woodstock ’94, the anniversary mega-concert in Saugerties, N.Y. Years of notorious hard living had turned Waylon Jennings into a protective father, and he wouldn’t allow it. But as a consolation, he ordered the concert on pay-per-view.

The entire family ended up bonding over a performance from Shooter Jennings’ favorite new band, Nine Inch Nails. (“And my dad fell in love with Primus,” he adds.)

If his latest music is any evidence, Jennings still holds Trent Reznor’s cathartic howl as a prime influence – certain tracks on “Black Ribbons” mimic Nine Inch Nails down to the snarling Reznorian vocal tics.

Upon graduating from high school, he was itching to take his music toward the brighter lights of a bigger city. So when he and his band Stargunn headed to Hollywood, he says he wasn’t trying to flee his father’s shadow in Nashville so much as migrate to a scene that spawned his rock ’n’ roll heroes.

But by 2003, Stargunn had split up and Jennings was mourning the death of his father, who had lost a fight with diabetes in 2002. The young songwriter had to reassess who he was and where he was headed.

He returned to music in 2005 with his solo debut and followed up with “Electric Rodeo” in 2006 and a more traditional album, “The Wolf,” in 2007 – each release gaining less and less traction.

By the end of 2007, Jennings found himself on the cusp of another identity crisis.

“I had let go of my management, I had let my label go,” he says. “They really collapsed the walls on me, and I had to dig out and figure out who I was.”