In July, 2001, Jim Florentine released Terrorizing Telemarketers Volume 1. After numerous plays on the Howard Stern Radio Show, his CD ranking on Amazon.com went from 282,363 to number 2. The only artist ahead of him was the Backstreet Boys. Later that week his CD came in at on the Internet Billboard charts.
After the release of Terrorizing Telemarketers Volume 2 in late 2001, Jimmy Kimmel and Adam Carolla took a liking to his prank calls and hired him for a show to debut in June 2002 on Comedy Central called Crank Yankers. Jim voiced Special Ed, a mentally retarded 16-year-old, and Bobby Fletcher, a rude and insulting man and Ed's older cousin.
After season 1, Eminem took a liking to Jim's characters and flew him out to his Detroit studio to do prank calls together for the upcoming season of Crank Yankers. The following year in 2004 Eminem and Jim did a bit together on the MTV Music awards show where Eminem beat up Special Ed. Crank Yankers lasted 3 seasons on Comedy Central. The show moved over to MTV2 in 2006 for one season. Jim's Special Ed character that he created is still played at various Sporting Events at stadiums across the USA.
Jim was featured on the series premiere of Down and Dirty with Jim Norton, a stand-up comedy series that aired on HBO on October 3, 2008. The series spotlights new and established talent, including Artie Lange, Bill Burr (Chappelle Show), Patrice O’Neal (Scary Movie 4) and Andrew Dice Clay. Lemmy, leader of the heavy metal band Motörhead, serves as musical director.
He is also co-hosting That Metal Show on VH1 Classic with Eddie Trunk and Don Jamieson. The show has been picked up for a fifth season.
Florentine just finished filming an independent dramedy, A Little Help, starring Jenna Fischer (The Office).
Florentine has been seen on The Apprentice, Comedy Central's Mother Load, HBO's Inside the NFL, Late Late Show with Craig Kilborn, The Opie and Anthony Show, The Howard Stern Show, Spike TV’s Video Game Awards, MTV Music Video Awards, Jimmy Kimmel Live, Last Call with Carson Daly, Tough Crowd with Colin Quinn on Comedy Central, VH1's The List, and Louie Anderson's Comedy Showcase. He also voiced the redneck radio host Bobbie Ray in the video game Grand Theft Auto: Vice City Stories.
He has a series of prank call CDs known as Terrorizing Telemarketers Volumes 1-5. The CDs feature a series of recorded telephone conversations, often with Florentine receiving calls from telemarketers, wherein he turns the tables on often aggressive salespeople by being deliberately difficult and creating awkward situations.
Florentine is currently touring the country performing solo and with Don Jamieson and is part of The Killers of Comedy tour.
In 2004 Jim worked one season on HBO Inside The NFL performing various comedy sketches. The show won an Emmy that season and Jim has proudly said in various interviews that when he was single he kept in on his night stand and it would close the deal anytime he had a date over. He called it his "Mariano Rivera".
At the same time Jim released two hidden camera DVD's called Meet The Creeps were him and partner Don Jamieson pull outrageous pranks on people including going to an all you can eat buffet and pulling their chairs right up to the buffet and eating from it. The DVD"s got in the hands of some Comedy Central executives and they brought Meet The Creeps to their Broadband Channel called Motherload. After the two successful seasons Comedy Central did a Meet The Creeps pilot for the network. The pilot was deemed too mean spirited and the show never made it on the network.
Between 2004 and 2008 Jim made 3 appearances on Jimmy Kimmel live on ABC. He also did appear on the Late Show with Craig Kilborn and Carson Daly. In 2007 Jim appeared on last episode of The Apprentice season 4 doing his edgy stand up comedy at a conservative charity event. He asked Trump's partner George if he wears a diaper. He has not been asked back on the apprentice since.
In 2008 Jim made an appearance on HBO's Down and Dirty Show with Jim Norton. Later that year That Metal Show which Jim hosts made its debut on VH1 Classic. It's described as The Tonight Show for AC/DC fans. As of Feb. 2010 it just got picked up for season 5.
Jim is an occasional guest on the late-night Fox News Channel show Red Eye w/ Greg Gutfeld, airing at 3 am ET.
Later in 2010 Jim will be in the feature film called "A Little Help" starring Jenna Fischer and Chris O'Donell. Jim plays Jenna love interest in the film.
