Max Greenfield has a habit of being in the right place at the right time. Since his network television debut in January 2005 as smirking Officer Leo on the cult hit Veronica Mars, Greenfield has been making like Forrest Gump and showing up in some pretty impressive places--as Rebecca Romijn‘s tart-tongued assistant Nick Pepper on Ugly Betty and in a memorable turn as the young Sandy Cohen on The O.C.

Now he’s appearing in a gay role, Michael, Calvin’s older love interest, in a multi-episode story on the ABC Family Channel’s breakout hit Greek, about the lives of a group of frat-and-sorority-bound college students. This Monday, Greenfield even shares a couple of surprisingly steamy kisses with Calvin’s Paul James.

The parts have sometimes been small, but it’s been impossible not to notice the handsome actor with the seductive voice and killer smile.

“It’s luck,” Greenfield tells AfterElton.com of his Zelig-like ability to land supporting roles in water-cooler shows. “I got Veronica Mars at a really, really lucky time. I didn’t even think they would pick up the whole season, and then the show kind of took off.”

Greenfield as Nick Pepper on Ugly Betty (left)
& Deputy Leo on Veronica Mars

For whatever reason, he’s been on a winning streak lately. Even his rejections seem to have been for a reason; his latest roles on Ugly Betty and Greek came, ironically, after auditioning, and being rejected by the producers, for the roles of Henry and Evan, respectively. “They kind of just remembered me, liked me, and thank God had a little bit of faith in me that I could do it,” Greenfield says.

But more prominent roles have meant increased attention for Greenfield, who is the object of multiple fan websites and whose heartbreaker good looks have been the subject of plenty of online discussions, including here at AfterElton.com.

“It’s completely flattering,” Greenfield says. “I think the best part about it is my Mom would go on the Internet and see all these things, and I think it gives her more faith that my career is going well and that I’m actually doing okay. I mean, it gives solace to my mother, which is nice.”

A smile that sweet, and he even thinks of his mother? Can Max Greenfield really be this nice?

No Plan B

Greenfield grew up in Dobbs Ferry, just north of New York City. He went to college in New York as an art major, but by the end of his first year, he had a feeling it wasn’t the right place for him to be. “I was burned out on painting,” he says.

His family had since moved to Los Angeles, so he followed after them. He had never considered a career as an actor, but found himself wondering if it wasn’t something he should try.

“The Los Angeles culture is just so inundated with it,” Greenfield says. “I was just kind of like, well, you know, why don’t we try this out?”

He took acting classes, and his first work was as an extra, which he hated.

“And then a few years later, I’m like, now I’m screwed,” he laughs. “I can’t go back to New York. I didn’t have a Plan B.”

But he gradually found more substantial work, on MTV’s steamy college soap opera Undressed—also a training ground for fellow hunks Adam Brody (The O.C.), Darryl Stephens (Noah’s Arc), Brandon Routh (Superman Returns), Bret Harrison (Reaper), and even Ugly Betty’s Michael Urie.

Next came parts on Gilmore Girls, Boston Public, Sleeper Cell, and his “big break” on Veronica Mars. He even had a short-lived show of his own on the WB, Modern Men, that was cancelled when the network lost time-slots by merging to become The CW.

Greenfield is reluctant to say he’s “made it,” but he’s optimistic about the future of his career. “I think I definitely would be ready to do something a little bit more substantial,” says the 28 year-old actor. “I’m in a weird age range. You wouldn’t buy me as a doctor or lawyer yet, but I’m also not in high school anymore.”

So what’s next for an actor with all this buzz and momentum, someone who seems to be on the verge of breakout stardom?

A gay role on Greek, of course.

Next Page! Gay kissing on Greek, and Max gives AfterElton.com some love!