"I graduated high school, I went on tour, album came out, tanked," recalled Levine. "We were dropped, I think, before the end of the year.
"It was terrible. We failed. And we were young and we thought we were off to the races. We thought we were big time."
Undeterred, they re-grouped and went in search of a different label under a different name: Maroon 5.
So where did the name "Maroon 5" come from? "You'll never know the answer to that question," replied Levine.
"Is it really that secret?" asked Cowan. "It's a secret, yeah."
Flynn added, "I don't even know. I don't really care, but I don't know."
Actually, Levine, admitted, the story of the band name origin is "depressing." "Yeah, it's so bad that we had to shroud it in the mystique of just never telling anybody."
With their new name, Levine found new songwriting inspiration, too, in a girl named Jane.
"What was great for that first record was, it was the first time my heart had been broken," said Levine. "And as a writer, as much as it sounds awful to say, that's gold (laughs)!"
Gold, indeed. In 2005, "Songs About Jane" won Maroon 5 a Grammy for Best New Artist of the Year. Levine called the win "the trippiest thing."
A track from "Songs About Jane" also won a Grammy in the Category of Best Pop Performance by a Duo or Group with Vocal. And Maroon 5 won a third Grammy in 2007 for the song, "Makes Me Wonder."
Two albums and two Grammys later, Maroon 5 hit dance floors everywhere with "Moves Like Jagger." It was the first time they had collaborated with other songwriters, and it went on to become one of the bestselling singles of 2011.
The once-shy songwriter was now baring it all, literally, showing off his ever-increasing collection of tattoos, like the number 222. "Yeah, that's my lucky number. Some of them mean something, but most of them don't."
While his music was well-known, Levine himself wasn't. But then came Reality TV. As a celebrity coach on NBC's "The Voice," Levine began rocking a whole new set of fans.
"Up until that point, people had seen you as a motorcycle-riding, sports car-owning, guitar-playing band member that actually had a lot of incredibly gorgeous girlfriends, and that's sort of where it ended," said Cowan.
"As much as I'm very private and guarded in certain ways, I feel like, yeah, ['The Voice'] was a chance to kind of put myself out there in a different way," said Levine.
This past week, he caused a stir by muttering "I hate this country" under his breath when it appeared two of his singing contestants were on the chopping block.
Levine later tweeted it was just a joke, but it's not the first time his mouth has gotten him in trouble.
"I'm very much OK with who I am and comfortable in my skin enough to embrace that, even though I don't say everything the right way and tend to be a bit impulsive with some of the words that I select," he laughed.
He is a fierce competitor -- especially with fellow coach Blake Shelton.
Theirs is dubbed the "bromance" of Reality TV. "Neither one of us takes ourselves that seriously," said Shelton. "And that's why we get along. That's why we are able to give each other crap and still come back here and laugh about and have a drink after the show."
As career decisions go, "The Voice" was a high note. Levine says the show has made his fan base "very big" -- big enough to launch a budding acting career, appearing on "American Horror Story."
And then there's the merchandizing, including an upcoming clothing line at K-Mart, as well as a celebrity fragrance he unveiled earlier this year in New York: "You know, it's the butt of a joke,"
he said. "Celebrity fragrance is a punch line. I know that. I know that!"
But he's not about to pass up opportunities, either.
"Capitalism is not my enemy. I am cool with doing things and trying things and thinking in a real kind of uniquely entrepreneurial way," Levine said. "Like, I love that. I don't shy away from saying that at all."
"So how long do you think you can keep up this pace, though?" asked Cowan.
"Not too much longer," he laughed.
His band even jokingly titled their latest album "Overexposed."
While it's more than he ever expected, being everywhere these days seems to suit him just fine.
"I'm constantly surprised at how long this has lasted -- I was expecting it to be over a few years ago," he said.
"Are you enjoying it?" asked Cowan.
"Yeah, Hell yeah, a lot! I just need a vacation."
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