Phil Leshing, the TV character

From Pop Matters:

LOVE MONKEY
Regular airtime: Tuesdays 10pm ET (CBS)
Cast: Tom Cavanaugh, Jason Priestley, Larenz Tate, Christopher Wiehl, Judy Greer, Ivana Milicevic, Eric Bogosian

A hip, sophisticated look at the music business and the love lives of four 30-something New York guys is not what you expect from CBS. But Love Monkey is an anomaly, an intelligent, well-written dramedy for adults about adults, even if some of the chords it hits are in a minor key.
Any worries that this series would be a High Fidelity knock-off were quickly put to rest in the first episode. Love Monkey plays like a smooth jazz record. The music business setting alone makes it fascinating: I can't think of a show that loved music this much since WKRP in Cincinnati. Still, with a plot based on four longtime friends who analyze their personal lives and maneuver through the singles scene invites comparisons to Sex and the City.

Based loosely on Kyle Smith's 2004 best-selling "guy-lit" novel, Love Monkey focuses on very nice guy Tom (Tom Cavanaugh), who seeks perfect music, perfect love, perfect friendships. In the midst of his quests, he lives the type of idealized Manhattan life that's found only on TV and in movies. And he's full of contradictions. A successful A&R rep for a "giant, chart-topping label" called Goliath, he pronounces in voiceover that "money should not be the goal" of his business. He's dating a vain, pretentious singer whose music he despises. Is it any wonder he can't commit?

Still, Tom's on a roll when we first meet him. He has signed 12 bands in a row and has his sights on an up-and-coming singer/songwriter named Wayne (Teddy Geiger), a John Mayer clone whom Tom believes is the next big thing. But during a staff meeting, Tom inexplicably has a Jerry Maquire-style meltdown, ranting that "money shouldn't be our goal" in front of the CEO. He's promptly fired, after which his girlfriend dumps him, and he learns that Goliath is close to signing Wayne.

Tom's realization that he just may be a self-centered jerk is the central problem to this otherwise thoughtful show. It's hard to believe that a guy this decent could maneuver through the shark-infested waters of the music business and still be successful, particularly when everyone else is a moneygrubber. This is particularly true of Tom's boss at Goliath, named Phil Leshing in an obvious homage to Grateful Dead bassist Phil Lesh (and sharply played by Eric Bogosian in a too brief appearance).

Cavanaugh brings the same aw-shucks, self-deprecating appeal he showed in Ed, which means Tom is more like the guy who'd share a joint with you at a concert than the exec angling to sign the band. Less convincingly, his niceness pays off: at the end of the first episode, after losing his job at Goliath, Tom finds a new one at the significantly named True Vinyl Records, where the team values music before money (and who steals Wayne away from Goliath). Here he also meets Julia (Ivana Milicevic), a free spirit who loves music as much as Tom.

The characterizations of Tom's friends are also formulaic. In the pilot, Tom says they "serve to remind me of all the things I've yet to accomplish." Yet, aside from their lack of achievement, we learn little about them. Mike (Jason Priestley) is married to Tom's sister and has a baby on the way; Jake (Christopher Wiehl) is a former pro baseball player turned sportswriter, and Scooter (Larenz Tate) is "a man about town." They're Tom's support group, constantly reminding him what a great guy he is.

Only Bran (Judy Greer) has the gumption to tell him to grow up. She obviously has deeper feelings for Tom, but makes up a story about a boyfriend rather than reveal them. Greer, so funny on Arrested Development, is underused here, but brings intelligence and vulnerability to a role that could easily slip into cliché. Potentially more interesting, Jake has a secret. When he's hit on by a former female conquest, he declines her advances, stating that he's not ready to date. But he speaks to her from behind a chain-link fence, giving him a look like he's in prison. It's not hard to figure what he's hiding, and it promises that the show will expand beyond Tom's world into the lives of his friends.