As Jeff Hardy's time in WWE comes to a close, experience the dizzying highs and soul-crushing lows of The Charismatic Enigma, courtesy of the September issue of WWE Magazine, on newsstands now. Get yourJeff Hardy gear at WWE Shop 

June, 25 1994
A scrawny kid with the nondescript white tights and bleach-blond butt-cut steps into the ring for the first time. Believe it or not, it was The Extreme Enigma making his WWE debut at the tender age of 16. Check out Jeff Hardy Videos

Oct.11, 1998
After nearly half a decade spent with their shoulders on the mat, Jeff & brother Matt—newly dubbed "The Hardy Boyz"—are rewarded with full-time WWE contracts. Check out Jeff Hardy Photos

June 29, 1999
Under the tutelage of Freebird Michael "P.S." Hayes, Jeff & Matt begin a Tag Team Championship campaign that culminates in an upset win over The Acolytes, earning them the first of many World Tag Team Championships. Matt Hardy Photos

Aug. 9, 1999
After former disciples Edge & Christian hit Gangrel with the metaphorical silver bullet, he recruits The Hardys to form The New Brood. Jeff & Matt ditch Michael Hayes and opt for an even darker, more intense WWE existence.

Relive some of Jeff & Matt Hardy's most exciting matches at  WWECLASSICS.com

Oct. 17, 1999
At No Mercy, The Hardys & Edge & Christian set a new standard for Ladder Matches with never-before-imagined acts of bravery, innovation and total disregard for bodily harm. Jeff and Matt win the match along with $100,000 and the managerial services of Terri Runnels. More importantly, they win a standing ovation from the crowd.

May 26, 2000
WWE Diva Lita begins her association with Jeff & Matt Hardy when they save her from an assault by former charge Essa Rios. Lita's in-ring ability is a perfect fit with The Hardys' style. Together, they form Team X-treme. Photos of WWE Alumni Lita

Aug. 27, 2000
Jeff wows audiences by stealing the show during the first-ever TLC Match at 2000's SummerSlam in his home state of North Carolina. WWE in Flight 

April 12, 2001
Jeff wins his first singles title—the Intercontinental Championship—after a huge upset on SmackDown. His opponent? Triple H. Jeff's improbable victory over The Game proves that he has what it takes to hang with WWE's top Superstars. Videos of The Game | Photos of The King of Kings

Dec. 9, 2001
A rift between the Brothers Hardy expands to gorge-sized proportions. The spat culminates in a Brother vs. Brother Match at Vengeance featuring Lita as the guest referee.

July 1 2002
After being brutalized by Undertaker for nearly 30 minutes in a Ladder Match, Jeff refuses to acknowledge his defeat as anything more than a technicality. But Jeff wins something just as valuable as a title—The Deadman's respect. Undertaker returns to SmackDown

April 23, 2003
Jeff's erratic behavior becomes a cause for concern. He's released from his contract and won't be seen in WWE for more than three years.

Aug. 4, 2006
Jeff Hardy re-signs with WWE. During his onscreen return to Raw (Aug 21, 2006), Jeff interrupts then-WWE Champion Edge &Lita, who had just thrown John Cena's spinner belt into Long Island Sound. Classic Jeff Hardy Photos

April 1 2007
Jeff competes in his first and (so far) only Money in the Bank Ladder Match at WrestleMania 23 and annihilates Edge from atop a ladder.

April 2, 2007
The day after WrestleMania 23, Jeff & Matt win a 10-Man Battle Royal for their sixth World Tag Team Championship.

Dec.16, 2007
Jeff enters the main-event picture by defeating Triple H at Armageddon to become the No. 1 Contender for the WWE Championship.

Dec. 31, 2007
Randy Orton kicks Matt Hardy in the head, taking him out of action. Jeff later retaliates by Swanton Bombing The Viper from a 20-foot-high scaffold.  

June 23, 2008
Jeff Hardy is moved to SmackDown as a result of the annual WWE Draft. Full SmackDown coverage

Nov. 14, 2008
Jeff spends months fighting for the WWE Championship but fails to capture gold. In response, he begins wearing war paint, evolving into a darker, more extreme Superstar.

Dec.14, 2008
At Armageddon, Jeff Hardy achieves the impossible, winning his first WWE Championship in a Triple Threat Match.  Hardy's 2008 Armageddon Photos

Jan. 9, 2009
The night before this SmackDown show, a mystery assailant runs Hardy off the road, but Jeff is unharmed.  One week later, making his entrance atop the SmackDown runway, a pyrotechnic mishap engulfs Hardy in flames.   

Jan. 25, 2009
The unthinkable happens! Matt Hardy turns on his brother Jeff at the Royal Rumble, and costs The Enigma the WWE Championship against Edge. Photos of Jeff Hardy at Royal Rumble  

April 5, 2009
Matt defeats Jeff in an Extreme Rules Match at The 25th Anniversary of WrestleMania, and five days later in a Stretcher Match on SmackDown. Check out Hardy's Dueling Diaries from the 25th Anniversary of WrestleMania Day 1 | 2 | 3 | 4 | 5 

April 26, 2009
Jeff finally exacts revenge on Matt by making him utter the words "I Quit" at Backlash and Swantons him through a table for good measure.  "I Quit" Photos

June 7, 2009
Jeff competes in a record-setting 14th WWE Ladder Match and defeats Edge to win his first World Heavyweight Championship. He then loses the title moments later when CM Punk cashes in his Money in the Bank opportunity, and drops Hardy with two GTS. Photos from Ladder Match at Extreme Rules

July 26, 2009
The Charismatic Enigma reigned supreme over CM Punk at Night of Champions to recapture the World Championship in heroic fashion. Night of Champions Main Event Photos

Aug. 23, 2009
Hardy battles CM Punk in an incredible TLC Match, ultimately losing the coveted World Title to The Straightedge Superstar for the second time. Photos of SummerSlam Main Event

Aug. 28, 2009
After a brutal Steel Cage Match with Punk for the World Heavyweight Championship, Jeff Hardy is forced to leave WWE, going out the way he lived his entire career, in the Extreme and on the edge. Watch Steel Cage Match | Watch Jeff Hardy's goodbye to WWE | Match Photos