My conversation with Jim Florentine begins with mass confusion.

"I can do a call-in whenever you want," he says in a burly, deep New Jersey monotone.

"Oh, good," I reply. "How does right now work?"

"What, are you gonna tape it?"

"Um… yeah?" I say hesitantly. (Don't most journalists tape their interviews?) "Yup… just gonna tape it over the phone here and do my little story."

"All right. I'll call back in about 20 minutes," he intones.

"Okay…"

When he calls back two hours later, I'm appreciative, if slightly panicky beneath the shadowy loom of my approaching deadline.

"Hi! It's great to talk to you," I say cheerily. "First off, how long have you been pulling your telemarketer pranks?"

Silence.

This is going badly.

"So we're gonna do the interview right now?" he asks.

"Well, yeah… Is now not a good time?" I'm getting a bit flustered at this point."

"No, now's great. I just thought you were gonna go into your radio voice or something."

For an agonizing moment, I wonder if maybe, just maybe, Florentine is fucking with me. It's the thing he is most notorious for, forging a career out of a series of comedy albums (Terrorizing Telemarketers, Vol. 1-4) and through the mouths of puppets on the Comedy Central cult hit, Crank Yankers. On the track "No No" off of Terrorizing Telemarketers 4, Florentine phone-talks an unassuming debt consolidator into circles, asking her to repeat a phantom sentence from her scripted sales pitch. "No, not that," he says. "The thing you said before that." "I have my script right here," she protests, "and there's nothing before that!" Their back-and-forth goes on for an uncomfortably, hilariously long time, and while I'm pretty sure I'm not immersed in a similar scenario myself, I've listened to enough of Florentine's particular handiwork to know his greatest gift is sounding completely earnest.

Then the moment passes, and I realize that Florentine simply thinks I'm a radio disc jockey and that we're on the air. I wonder ever-so-briefly what would happen if I just went with it--if I did pretend to be a DJ and affected some smooth vocal cheese for our imaginary live interview. But I don't think I could hang with Florentine, who seems a master of vocal control and understatement. In another of his preposterous telemarketer riffs he befuddles an inquiring phone service rep for minutes on end, trying to coordinate a multi-line conversation with two other, extremely busy, and more importantly, fictitious roommates ("Threesome," Terrorizing Telemarketers Vol. 2). The prank shouldn't even work, let alone go on forever, but Florentine's utterly natural delivery saves the day.

Florentine's vocal tricks also include incredibly loud and disgusting burps, and talking like a very excitable retarded person--both of which are used to maximum effect during his phone exchanges. On Terrorizing 3 he parries a cell phone salesman's every verbal lunge with his now-signature line, "Yay!" ("Yay! I'm gonna get a free cell phone!" "Yay! If I don't like it I can get it canceled! Yay!"), and on the Crank Yankers skit, "Bobby Fletcher Calls for a Job," he relentlessly interrupts a blue-collar manager's job description with a colorful slew of wet belches.

"I never thought I'd pay my mortgage goin' 'yay!' and burpin'," Florentine says, once our initial mutual confusion has been straightened out. "God bless America!"

A struggling comedian for over a decade, it never occurred to Florentine that his penchant for manipulating telemarketers--which he's done since he was a little kid-- was pure comic gold. One day, a friend asked to listen in on the other line, realized the brilliance of what he was doing, and convinced Florentine to send a tape of it to the Howard Stern Show.

"It was on the air the next day," he says. Four years later, Florentine is a Stern staple, in the thick of a 40-stop summer tour with other Stern comedy stalwarts Craig Gass, Rev. Bob Levy, Sal the Stockbroker, and Beetlejuice. Tragically, Florentine won't be pranking telemarketers in the live setting ("You gotta go through, like, 10 of them before you get one worth listening to."), nor will he sport one of the puppets from Crank Yankers ("I don't have time to work a puppet onstage, I'm too busy jerkin' off."), but he tells stories about the pranks in his standup act, and also shares deadpan, discomfortingly honest personal anecdotes.

"That's the direction comedy's going in right now--kinda edgy, kinda brutal. But it's huge right now. Comics are filling out arenas like rock stars or something. People are sick of the mediocre crap the networks try to sell you as comedy. Nobody wants to see that corny crap anymore. I just like doin' standup."

4 Men & a Baby, with Howard Stern Show comedians Jim Florentine, Craig Gass, Rev. Bob Levy, Sal the Stockbroker, and Beetlejuice, plays at the Aladdin, 3017 SE Milwaukie, Saturday July 9, 7 & 10 pm, $20