Edge was then placed in a feud against the vampire wrestler Gangrel. During the feud, Gangrel introduced Christian Cage (now going by just "Christian"), Edge's storyline brother, as his ally. Eventually, Gangrel and Christian convinced Edge to join them, and the three of them formed an alliance known as The Brood. The Brood as a whole was later abducted by and converted into The Undertaker's Ministry of Darkness. In May 1999, the Brood broke away from The Ministry after Christian was attacked by Ken Shamrock and forced to reveal the location of the captive Stephanie McMahon. The Undertaker chose to have Christian punished for his trespass, but Edge and Gangrel stood by him and betrayed The Undertaker leading to a brief feud with the Ministry.
Edge captured his first singles championship, the WWF Intercontinental Championship, on July 24, 1999, defeating Jeff Jarrett at a house show in Toronto, Ontario. He lost the title the next night to Jarrett at Fully Loaded.
Later in the year, he was placed in a storyline angle with The Hardy Boyz (Matt and Jeff). Soon, however, Gangrel betrayed both Edge and Christian and formed The New Brood with their enemies, The Hardy Boyz. They feuded with the Hardy Boyz, as they went onto compete in a ladder match at No Mercy in October for the "managerial services" of Terri Runnels and USD$100,000, which the Hardy Boyz won. At WrestleMania 2000 on April 2, Edge and Christian defeated the Hardy Boyz and the Dudley Boyz (Bubba Ray and D-Von) to win the WWF Tag Team Championship in a Triangle Ladder match, which ultimately led to the creation of the Tables, Ladders, and Chairs match (TLC).
Following this victory, Edge and Christian found success as a villainous duo, shifting their in-ring personas from borderline goth to a comedic pair of "cool dudes", winning the WWF Tag Team Title six more times (for a total of seven). During this time, their trademark became the "five second pose" where they performed a pose in the ring for five seconds "for the benefit of those with flash photography" to mock, insult, or otherwise amuse the fans. They also competed as a team in the first three Tables, Ladders, and Chairs matches, winning the first two over The Dudley Boyz and The Hardy Boyz, at SummerSlam in 2000 and then again at WrestleMania X-Seven. At the 2001 Royal Rumble, Edge and Christian were defeated by the Dudley Boyz and lost the World Tag Team title. They unsuccessfully attempted to regain the tag team title at No Way Out against the Dudley Boyz and the Brothers of Destruction (The Undertaker and Kane), but they succeeded at WrestleMania X-Seven against the Dudley Boyz and The Hardyz in the second TLC match.
Edge went on to solidify himself as an emerging singles competitor by winning the King of the Ring tournament in 2001. Edge eventually became a fan favorite during the Invasion storyline. Christian betrayed Edge shortly afterward, and the two feuded over Edge's Intercontinental Championship that Edge won at SummerSlam and later lost to Christian at Unforgiven, though, Edge captured the title later. Following this, Edge lost the Intercontinental title to Test and shortly afterwards won the WCW United States Championship from Kurt Angle. Edge defeated Test at Survivor Series to unify the Intercontinental Championship with the U.S. Championship. Throughout mid-2001, Edge was placed in a feud with William Regal for the Intercontinental Championship. Edge, however, came up short in the feud.
The following year, at WrestleMania X8, Edge found himself in a match with Booker T that was the result of Edge beating out Booker for a fictitious Japanese shampoo endorsement. Shortly after defeating Booker T at WrestleMania, Edge was drafted to the SmackDown! brand in the first WWE Draft Lottery. Upon arriving there, he began a feud with Kurt Angle, which culminated in Edge shaving Angle's head following a hair vs. hair match at Judgment Day. Edge and Rey Mysterio formed a partnership, which ultimately resulted in the two capturing the newly established WWE Tag Team Championship on November 2, 2002. Their reign lasted fifteen days. Edge, however, would go on to recapture the World Tag Team Championship (renamed WWF Tag Team Championship) alongside Hulk Hogan that year.
In February 2003, Edge suffered a legitimate neck injury and had to undergo surgery with Dr. Lloyd Youngblood. Recovery kept him sidelined for close to a year. He was placed on the Raw brand in the WWE Draft after WrestleMania XX and returned to in-ring action shortly after that event. On the April 19, 2004 episode of Raw he and Chris Benoit won the World Tag Team Championship. They continued a close partnership even after losing the title, but it was disbanded when Edge won the Intercontinental championship at Vengeance from Randy Orton. Following a legitimate groin injury in a non-televised match, Raw General Manager Eric Bischoff stripped Edge of the Intercontinental title.
Upon his return, Edge, Chris Benoit, and Shawn Michaels received a title shot for Triple H's World Heavyweight Championship at Taboo Tuesday in October 2004. Michaels won the audience vote to receive the title shot, giving Edge and Benoit a tag team title shot. During the match, Edge abandoned his partner (although Benoit managed to win the title on his own) and instead interfered in the main event, costing Michaels the championship. On the November 1 episode of Raw, Edge and Benoit lost the World Tag Team Championship with Edge once again abandoning Benoit and sitting in a chair and watching the match. After the conclusion of the match, Edge attacked Benoit. In November episode of Raw, both Edge and Benoit competed in a number one contender's battle royal, but they eliminated each other simultaneously at the conclusion of the match, resulting in a draw. As a result, Triple H was forced to defend the title in a triple threat match. In the match, Benoit locked on the Crippler Crossface on Edge, who shifted his weight putting Benoit's shoulders on the mat for a pin. This match also ended in a draw for Benoit and Edge, as Benoit made Edge submit at the same time the referee counted a pinfall for Edge. As a result, the World Heavyweight title was vacated the following week on Raw.
In January 2005, Edge competed in his first Elimination Chamber match at New Year's Revolution for the vacant World Heavyweight Championship. Shawn Michaels (acting as special guest referee) would perform a superkick on Edge, in retaliation for an accidental spear by Edge, causing Edge to be the first eliminated. This led to a match at the Royal Rumble later in the month, in which Edge defeated Michaels. Subsequently, at WrestleMania 21, Edge won the first ever Money in the Bank ladder match, gaining himself a contract that gave him a shot at the World Heavyweight championship within one year.
Even though he was already a villain, Edge faced even more scorn from the fans due to his adulterous affair with WWE Diva Amy Dumas, known on-screen as Lita. Dumas had been the girlfriend of Copeland's close real-life friend, Matt Hardy. When Dumas suffered a torn anterior cruciate ligament, she was put out of action, and it was during this time that Copeland began an affair with her while she was still in a relationship with Hardy. Shortly after the incident became public knowledge, WWE released Hardy resulting in even more backlash towards Copeland and Dumas. After Hardy returned, however, the real-life situation was translated into a storyline.
Edge was then paired with Lita in an angle where she betrayed her storyline husband Kane, which ended with a stretcher match that Edge won, but shortly before, Kane performed a tombstone piledriver on Lita. On the July 11 episode of Raw, Edge's match with Kane was interrupted when Matt Hardy made a surprising appearance. The situation was a real-life occurrence, with Hardy referring to Edge as "Adam" and issuing a threat to Lita as well. When Hardy was officially brought back to Raw, he and Edge continued their feud, including a match at SummerSlam where Edge defeated Hardy, causing Hardy to have "excessive blood loss". They also competed in a Street Fight, which resulted in a no contest when Hardy performed a side effect on Edge off the entrance ramp into the sound speakers and other electrical equipment. They also fought in a Steel cage match at Unforgiven in September that saw Hardy win. The feud culminated in a "Loser Leaves Raw Ladder Match" at WWE Homecoming on October 3, which Edge won, causing Hardy to move to the SmackDown! brand.
Shortly after the Homecoming victory, Edge suffered a legitimate torn pectoralis major muscle that kept him shelved for several weeks. During his time off, he starred in his own talk show segment on Raw entitled The Cutting Edge, dubbing himself the "Rated-R Superstar". Edge used his talk show to start a feud with Ric Flair following Flair's well-publicized arrest in connection with a road rage incident. Edge eventually began using The Cutting Edge as a soapbox to run down Flair until, after weeks of public mockery, Flair eventually showed up and attacked Edge.
Edge and Ric Flair formally met at the New Year's Revolution event in 2006 in a match for Flair's Intercontinental Championship, which resulted in Flair retaining, after Edge was disqualified. Later that night, after the conclusion of the main event match, the Elimination Chamber, WWE Chairman Vince McMahon appeared on stage and declared that WWE Champion John Cena had to defend the WWE Championship, after he just retained. As a result, Cena was forced to defend the title against Edge, who cashed in his Money in the Bank contract at that moment. Edge defeated Cena in less than two minutes after two spears to become WWE Champion for the first time. In an interview conducted after the event, on WWE.com, Edge announced that he and Lita would have "hot, nasty, sex" in the middle of the ring on Raw the following night to celebrate his victory. On Raw, Edge held up to that promise by engaging in foreplay with Lita until they were interrupted by Flair, who called Edge a disgrace and "dead in the bed". Flair, however, ended up on the receiving end of a con-chair-to on the announcers' table until Cena came out to Flair's aid and performed an FU on Lita. The "Live Sex Celebration" segment earned Raw a 5.2 rating, the highest Raw rating in over a year, leading Edge to call himself the "most-watched WWE Champion in the last 5 years".
Three weeks later, at the Royal Rumble, Edge lost the WWE Championship back to Cena. He then lost a return match on a special Thursday episode of Raw held in February. Edge blamed special guest referee Mick Foley for his loss, claiming biased officiating and attacked him. At Saturday Night's Main Event, Foley got revenge on Edge by assaulting him with a con-chair-to. They feuded until WrestleMania 22 in April, where Edge defeated Foley in a Hardcore match by spearing him through a flaming table, but suffered second degree burns.
Edge used his victory over Foley to once again challenge John Cena for the WWE Championship. Triple H was involved in a feud with Cena at the time, resulting in a triple threat match at Backlash, where Cena pinned Triple H to retain the title. After Backlash, Edge continued his feud with Mick Foley as they entered a triple threat hardcore match. Foley, however, betrayed his friend Tommy Dreamer with Edge's assistance. Edge and Foley then proclaimed that, because of their brutal match at WrestleMania, they were the true Hardcore Champions. At June's pay-per-view event One Night Stand, Edge, Foley, and Lita defeated Dreamer, Terry Funk, and Beulah McGillicutty in an Extreme rules tag team match. Later in the event, Edge interfered in the WWE title match between John Cena and challenger Rob Van Dam, helping Van Dam win the title. Edge, who won a number one contender's match for the WWE title to face Van Dam, was unable to win the title at Vengeance.
Two weeks later on Raw, Edge pinned Van Dam in a triple threat match, after blindsiding Cena with the title belt, to become WWE Champion for the second time. This angle re-ignited Edge's feud with Cena, and he lost by disqualification at Saturday Night's Main Event in order to retain the title. Subsequently, a match was made for the August event SummerSlam with the stipulation that if Edge disqualified himself, he would lose the title. At the event, Edge retained the title by pinning Cena after he hit him in the back of the head with a pair of brass knuckles, this occurred when the referee was not looking. The night after SummerSlam, Lita disposed of Cena's customized "spinner" belt into the Long Island Sound at Edge's command, who declared it the end of the "Cena era" in his life. Edge later unveiled the new "Rated R" version of the belt. Cena, however, interfered in Edge's match with a returning Jeff Hardy later that night, chasing him down to the outside of the building, assaulting him down, and tossing Edge into the Long Island Sound. The following week, Cena made a deal with Edge: if Edge could defeat him in a match for the WWE Championship, he would sign a contract to move to SmackDown!. Edge accepted, on the condition the match be a TLC match held at September's Unforgiven event in Edge's home town of Toronto. At the event, he lost the championship after Cena performed the FU on him, sending Edge crashing through two stacked tables from a ladder. At one point during the match, Cena locked in the STFU on Edge, who later said he was legitimately choked unconscious, the first time he had been knocked out in a match during his career.
On the October 2, 2006 episode of Raw, interference from the newly reformed D-Generation X (DX) (Triple H and Shawn Michaels) cost Edge his "final chance" at John Cena's WWE Championship in a Steel cage match, though their interference was a response to the interference of Lance Cade and Trevor Murdoch, led to Edge approaching Randy Orton and asking him to join forces to defeat DX, which Orton accepted and joined an alliance with Edge. The two formed the tag team Rated-RKO. Rated-RKO became the first to defeat DX since their reunion, and quickly dominated the Raw brand's tag team division to become tag team champions, making Edge a record holder of 11 World Tag Team Championship title reigns in his WWE career.
As part of the storyline angle, Rated-RKO attacked Ric Flair with steel chairs to enrage DX on November 27. At New Year's Revolution in January 2007, Rated-RKO faced DX in a title defense, but the match was declared a no-contest when Triple H suffered a legitimate injury during the match. With Triple H out of action, the team continued their on-screen rivalry with remaining DX member Shawn Michaels. Michaels teamed with John Cena to defeat Rated-RKO for the tag team championship on January 29, 2007. Edge and Orton suffered a series of losses to Cena and Michaels in the following months, building hatred towards one another. Edge and Orton also became rivals in their goals of achieving the WWE Championship. Neither Edge nor Orton won the championship, and they lost their claims as number one contenders after a failed match with Cena at Backlash in April.
On the May 7, 2007 episode of Raw, Edge defeated Mr. Kennedy to win his Money in the Bank title opportunity (Kennedy had suffered a legitimate injury prior to the match), making Edge a two-time Money in the Bank holder. On the May 11 episode of SmackDown!, Edge cashed in his newly won contract against The Undertaker, following Undertaker's title match against Batista in a Steel cage match. Following the match, a returning Mark Henry assaulted The Undertaker. Edge took advantage of the situation and defeated Undertaker with a Spear to win his first World Heavyweight Championship. As a result of this victory, Edge became a part of the SmackDown! brand. Edge then began a feud with Batista and successfully defended his championship title against him at Judgment Day, in a Steel Cage match at One Night Stand, and a third and final time in a last chance match at Vengeance. Edge then began a feud with Kane after SmackDown! General Manager Theodore Long announced Kane as the new number one contender for the World Heavyweight title. Edge was forced to relinquish the World title due to a legitimately torn left pectoral muscle injury on the July 20 episode of SmackDown! following an attack by Kane.
At November's pay-per-view event, Survivor Series, Edge made his return, interfering in a World Heavyweight Championship Hell in a Cell match between Batista and The Undertaker. The following SmackDown! show saw Edge and General Manager Vickie Guerrero make their relationship public, making his official in-ring return in a World title match against Batista on November 30, a match that ended after The Undertaker interfered. At Armageddon, Edge won the World Heavyweight Championship, after giving The Undertaker two chair shots and pinning the defending champion Batista (who had been Tombstoned by Undertaker prior) in a Triple Threat match. During the match, Edge used two look-a-likes to distract Batista and The Undertaker. It was later revealed that these look-a-likes were the Major Brothers, who were then repackaged as Curt Hawkins and Zack Ryder. Edge also formed an alliance with Chavo Guerrero, nephew of Vickie Guerrero, and on the January 22, 2008 broadcast of ECW, he assisted Chavo in winning the ECW Championship from CM Punk, even though Chavo previously rebuffed Edge and allied himself with Rey Mysterio, Edge's scheduled opponent at the Royal Rumble pay-per-view. The group eventually came under the name of La Familia.
At WrestleMania XXIV, Edge lost the World Heavyweight championship to The Undertaker when he tapped out to the gogoplata, a submission maneuver by Undertaker. In a WrestleMania rematch, The Undertaker defeated Edge once again at Backlash to retain the World Heavyweight championship. Following Backlash, The Undertaker was stripped of the World title by Vickie Guerrero and faced Edge for the title at Judgment Day in May and then again at One Night Stand in a TLC match in June. The first match ended with a countout victory for The Undertaker but no champion was crowned due to the circumstances. The second match at One Night Stand saw Edge walk away champion, which also meant Undertaker was banished from the entire WWE.
On the June 30, 2008 episode of Raw, Edge lost the World title to CM Punk, after Batista assaulted Edge and prompted Punk to cash in his Money in the Bank contract and defeated Edge to win the World Heavyweight championship. On the July 4, 2008 episode of SmackDown, Edge took his frustrations out on Vickie because he lost the title and told her the wedding was off. The following week, however, after Guerrero saved Edge from a con-chair-to by The Big Show, Edge re-proposed, and the wedding was back on. On July 18, 2008 at the wedding reception, Triple H came out and showed a video of Edge cheating on Guerrero the day before with the wedding planner, Alicia Fox. The angle continued at The Great American Bash in July, when Fox attempted to hand Edge the WWE Championship belt to use as weapon against Triple H, but was stopped by Guerrero. Edge attempted to spear Triple H but hit Guerrero instead, with the distraction, Triple H performed a Pedigree on Edge to retain the WWE title. Edge attempted to apologize to Guerrero, even though he was seen talking to Fox, but she revealed to him that she had rehired The Undertaker and that Edge would face him in a Hell in a Cell match at SummerSlam. Edge then turned on La Familia during the August 8 episode of SmackDown, performing a one man con-chair-to on Chavo in the ring, and tossed Guerrero out of her wheelchair, effectively disbanding the faction. The following week, Edge verbally assaulted Guerrero, before he forced her to apologize to The Undertaker for what she did to him. He also mentioned to Guerrero, that it was because of her that La Familia suffered. At SummerSlam, The Undertaker defeated Edge, and after the match, Undertaker chokeslammed Edge off the top of a ladder and through the ring canvas, with flames rising from the hole.
On November 23, 2008 at Survivor Series, Edge returned to WWE after an introduction by SmackDown General Manager and his on-screen wife Vickie Guerrero, replacing Jeff Hardy in the Triple Threat match for the WWE Championship involving champion Triple H and Vladimir Kozlov. He pinned Triple H to become the WWE Champion for the third time in his career. The following month, Edge lost the title to Hardy at Armageddon in a Triple Threat match, which also featured Triple H. At the Royal Rumble, however, Edge regained the title in a no disqualification match, following Matt Hardy's interference. At the February event No Way Out, Edge lost the WWE title in an Elimination Chamber after being pinned by Jeff Hardy, being the first to be eliminated, with the title eventually being won by Triple H. Later that night, Edge inserted himself into the World Championship Elimination Chamber match after attacking Kofi Kingston and barricading himself inside one of the Chamber's pods, proceeding to win his eighth World Championship, last eliminating Rey Mysterio and taking the title over to SmackDown. At WrestleMania XXV in April, Edge lost the championship to John Cena in a Triple Threat match, which also included The Big Show. Three weeks later he regained the championship at Backlash, when he defeated Cena in a Last Man Standing match, after interference by The Big Show. After a successful defense against Jeff Hardy at Judgment Day, he lost the title to Hardy at Extreme Rules in a ladder match, and afterwards said some disparaging things to his on-screen wife, Vickie Guerrero. The following night, Guerrero announced that she quit as the Raw General Manager due to being humiliated, and Edge came out to apologize. Instead, however, he claimed he married Guerrero because she had authoritative powers as the General Manager, and sought a divorce.
In June, Edge won the Unified WWE Tag Team Championship (the seeming unified version of the World Tag Team Championship from the Raw brand and the WWE Tag Team Championship from the SmackDown brand) with Chris Jericho at The Bash after he and Jericho were inserted into the match as late entries just prior. On July 3, Edge suffered a torn Achilles tendon while competing at a live event in San Diego in a match against Jeff Hardy, and later underwent surgery. He is set to return in 2010.