1. August 1994: Playboy.com becomes the first national magazine to go online. The initial site is an electronic store selling products like the Playboy Interview CD-ROM, an electronic datebook, coffee table books and a CD jazz collection. With no publicity, the site receives 10,000 hits in its first two days. CNN's Tech Guide Dennis Michael announces the site's debut by saying, "Your computer already has a mouse; perhaps what it needs is a rabbit." Within a year Playboy.com averages 800,000 hits per day.

2. November 1996: The members-only Playboy Cyber Club debuts with Playmate photo archives, Playboy Interview archives and multimedia features including real-time chats with Playmates. The technology can't accommodate the overwhelming traffic, and the site is temporarily closed down while it is reconfigured. The Cyber Club re-premieres in June 1997 with more than 10,000 photos and a virtual Playboy Mansion in which subscribers can roam through the 35-room manse and interact with models.

3. March 11, 1997: Playboy magazine takes advantage of the Web's timeliness and publishes its groundbreaking Timothy McVeigh article on Playboy.com, three months before it hits the newsstand (and three weeks before McVeigh's trial begins). Written by former Reuters reporter Ben Fenwick, "The Road to Oklahoma City" chronicles for the first time, in minute detail, McVeigh's actions the day of the Oklahoma City bombings. The article runs with the editor's note that it was based on "lawfully obtained documents" prepared for the defense and the disclaimer that its version "contains discrepancies with other published accounts of the bombing." The Playboy.com article makes worldwide news and is covered by the Associated Press, NBC News, CBS News, CNN, CNBC, the Washington Post and others.

4. December 31, 1997: Playboy.com broadcasts live, conducting its first webcast from Hugh Hefner's New Year's Eve party at the Playboy Mansion. Tina Bockrath, Miss May 1990, hosts the live audio feed and moderates an interactive chat with Playmates, celebrity guests and, of course, Hef. Cyber Club members are able to look around the party and save digital snapshots by using a robotic interactive camera.

5. March 1999: An army of Playboy.com photographers and producers descends upon the French Quarter in New Orleans for live dispatches from Mardi Gras. Playboy.com's annual coverage becomes the premier online destination to experience all of Bourbon Street's debauchery, with everything from survival guides to flasher galleries and sexy balcony shows featuring Playmates and models playing up to the crowds.

6. September 2000: The Cyber Club introduces "the next step in the evolution of men's entertainment," the Playboy Cyber Girl. Every Monday, Cyber Club members are treated to a sexy new Cyber Girl of the Week, and on the first Monday of each month members cast their votes for the Cyber Girl of the Month. The winning girl is photographed anew, with video clips and other surprises included in her profile. A number of Cyber Girls eventually become Playmates, going from the pixels of the Cyber Club to the pages of Playboy magazine, including inaugural Cyber Girl Stephanie Heinrich. Cyber Girl Carmella DeCesare goes on to become the 2004 Playmate of the Year.

7. December 2000: The site's Sexiest Sportscaster poll, titled "A League of Their Own," causes a huge sensation. Sports Illustrated calls it "the season's second most discussed poll," after the Bush-Gore race. (CBS's Jill Arrington narrowly beats out Monday Night Football's Melissa Stark for the honor.) Subsequent Playboy.com Sexiest polls continue to cause online pandemonium, including 2003's Search for America's Sexiest Meteorologist, which draws more than 650,000 votes.

8. July 2001: Playboy.com launches a full-screen television-style advertisement that the media heralds as being ahead of its time. The "Mega Unit" ad weds cutting-edge technology with the personality of Playboy's founder to create a killer animated commercial for Jack Daniel's. One critic writes, "At the end of the day, it's creativity that makes the difference.... Jack Daniel's on Playboy.com thought and executed literally out of the box."

9. October 2002: Marilyn Manson becomes the site's first Celebrity Guest Photographer when he photographs girlfriend Dita von Teese. The feature catches fire among A-listers. Celebs including Dale Earnhardt Jr., OutKast, Carmen Elektra and Nelly accept the invitation to strap on a camera and play Playboy photographer for a day.

10. November 2003: The Cyber Club's original Women of Wal-Mart pictorial makes a huge splash. The controversial pictorial, featuring six Wal-Mart employees from across the country rolling back their blue smocks, receives so much traffic on its first day that it briefly shuts down the site.