Raised in a stable home in Dallas, Loeb had all the advantages -- ballet, tap, piano, music theory, ice skating. Her parents encouraged her musical development and she was able to attend Brown University.
She could easily incorporate "I Got No Right to Sing the Blues" into her repertoire.
In a posting on her Web site (lisaloeb.com), Loeb conceded that a biography that her record label wrote for her was "boring," so she wrote one for herself.
"For every album that comes out, there's an over dramatic bio to go with it," she said. "I don't think I can tell any stories about how I lived in a van in Alaska."
She goes on to tell fans that she even had her own bedroom "most of the time" when she was a kid.
So darned stable. So organized. So centered.
Yet she can write, in "She's Falling Apart," about a young woman whose life is nowhere near as serene as it looks on the surface:
"And they rise in the morning/And they sleep in the dark/And even though nobody's looking/She's falling apart."
Or take "It Drops Me Down," in which Loeb sounds positively pessimistic:
"I walked away to get wisdom/But in the end I just walked home/And it drops me, drops me down/And I'm not feeling so good again."
Loeb dabbles in resignation at times too, such as in "Falling in Love":
"The time between meeting and finally leaving is/Sometimes called falling in love."
Don't get the idea, though, that Loeb doesn't look up sometimes, because she does. Consider this from "Truthfully":
"Truthfully, I really can't explain, I'm floating, I'm smiling again./ Truthfully, I can't ignore you, cause I've been waiting for you."
In concert, playing for committed fans, Loeb offers an image more in tune with the upbeat side of her music -- which, by the way, almost always feels upbeat even when the lyrics are about the downs.
In a recent appearance at the House of Blues in Hollywood, Loeb was assured and in command, practicing her craft with an almost white-collar professionalism traditionally associated with doctors and business executives -- while at the same time making the music emotionally accessible to her audience.
This is not an easy balancing act.
It seems entirely possible that Loeb is able to pull it off precisely because she brings that personal emotional balance to her work. It must also help that Loeb genuinely respects her audiences, as much as they seem to respect her.
"My fans tend to be intelligent, I think," said Loeb in an interview with United Press International.
Loeb said she often spends more than an hour talking to fans after her shows, and picks up signs that most of them have a fine sense of humor -- from the jokes they tell to the captions on their T-shirts.
"They are funny, earnest and sincere," she said. "I feel like my life sometimes is a big wedding or bar mitzvah where I'm meeting this big extended family."
Loeb said her relationship with her fans is "like a perfect give and take."
However, Loeb said touring has some downsides too.
For example, she doesn't like that younger fans can't get in when she plays "21 and up" clubs. She prefers events like the recent in-store appearance at a the Sanrio store in Times Square that attracted fans "of all ages, colors, gay, straight, Broadway fans, rock fans."
Sanrio was a natural place for Loeb to play to promote her latest album, "Hello Lisa." She is a huge fan of Hello Kitty, the character at the center of Sanrio's flagship line of merchandise.
"I've loved her since I was a kid. I've been collecting her stuff. I even use it now," said Loeb, pointing out the Hello Kitty watch on her wrist.
You see? Just so darned uncomplicated.
Really hard to write about.