On October 26, 1996, Angle attended the Extreme Championship Wrestling (ECW) High Incident event. He gave an in-ring interview and provided guest commentary during a match between Taz and Little Guido.
His first appearance on WWF television was on the March 7, 1999 episode of Sunday Night Heat, where he took part in an angle with Tiger Ali Singh. This angle involved Singh paying Angle money to blow his nose on the American flag. Angle instead blew his nose on Singh's flag and fought him off. His first WWF match was a dark match victory over Brian Christopher on April 11. In the following months, Angle wrestled on house shows and in other dark matches in preparation for his televised debut.
After several weeks of vignettes, Angle made his televised WWF in-ring debut on November 14 at Survivor Series at the Joe Louis Arena in Detroit, Michigan, defeating Shawn Stasiak. He began using The Patriot's theme "Medal" (also used once by Sgt. Slaughter) for his ring entrance, which became associated with Angle for the rest of his career. In his initial push, he remained undefeated for several weeks, eventually losing to the debuting Tazz by passing out at the Royal Rumble. Angle's television character was an "American hero" gimmick based on his gold medal win at the 1996 Summer Olympics. In his promos, Angle presented himself as a role model and stressed the need to work hard to realize one's dreams, stressing the 3 I's, "Intensity, Integrity and Intelligence". In his promos and ring entrances, Angle always wore replicas of his gold medals around his neck. While he stood for many principles that are associated with faces, Angle was noticeably booed in his debut match and even the next night on Raw Is War in his match against The Godfather, which took place in his hometown of Pittsburgh. The fans in general did not react positively to his billing as the first "real athlete" in the WWF, which ultimately led to him being portrayed as a heel, talking down to the audience and behaving as though he was better than the fans and fellow wrestlers, usually taunting them with the question of, "Where are your gold medals?"
Angle won both the European Championship and the Intercontinental Championship in February 2000, billing himself as the "Eurocontinental Champion". He dropped both of his titles without ever conceding a fall in a two falls triple threat match with Chris Benoit and Chris Jericho at WrestleMania 2000.
Throughout mid-2000, after aligning himself with Edge and Christian, "Team ECK" (Edge, Christian, and Kurt) feuded with Too Cool and Rikishi, with Angle defeating Rikishi in the finals of the 2000 King of the Ring tournament. He went on to feud with Triple H after a love triangle between them and Triple H's wife, Stephanie McMahon, developed. As a change to the intended storyline of Stephanie turning on her husband and going with Angle, he lost to Triple H at Unforgiven. Before the match started, however, he bumped into a returning Stone Cold Steve Austin, who was looking for the perpetrator who ran him over at the previous year's Survivor Series. Angle offered him his friendship and one of his gold medals, but Austin was not pleased by telling him that he would keep it in a nice safe place, to which Austin attacked Angle and threw his medal to the floor.
Following his feud with Triple H, Angle received another push and began pursuing the WWF Championship, defeating The Rock at No Mercy, after botched interference on The Rock's behalf from Rikishi. With his victory over The Rock, Angle became the first wrestler to have won both an Olympic Gold medal and the world championship. Angle retained the WWF Championship for the rest of the year in matches with The Undertaker at Survivor Series and in a six-man Hell in a Cell match at Armageddon. After beating Triple H at the Royal Rumble, Angle eventually lost the title to The Rock at No Way Out.
Angle then feuded with Chris Benoit whom he defeated at WrestleMania X-Seven, but lost to him at Backlash in an Ultimate Submission match; Benoit defeated Angle four falls to three in sudden-death overtime. Continuing the feud, Angle again defeated Benoit in a two out of three falls match at Judgment Day. Benoit pinned Angle after an Angle Slam in a "Pinfalls Only" fall, and then Angle made Benoit submit with the ankle lock in the "Submissions Only" fall. Angle won the third fall, a ladder match, with the help of Edge and Christian.
When World Championship Wrestling (WCW) and ECW were purchased by WWF, the wrestlers from both promotions joined and formed The Alliance and invaded the WWF in mid-2001 (dubbed as "The Invasion"). As a result, Angle turned face and began a storyline where he joined forces with WWF Champion Stone Cold Steve Austin to repel them. At Invasion, Angle and Austin captained a team of five WWF superstars against five handpicked members of the Alliance. As part of the angle, Team WWF lost to Team Alliance when Austin turned on his team to join The Alliance. At the close of the match, Austin nailed Angle with a Stone Cold Stunner, causing him to get pinned by Booker T. After winning and losing the WCW Championship, WCW United States Championship and the WWF Hardcore Championship in matches with Alliance members, Angle defeated Austin in a SummerSlam rematch to win his second WWF Championship at Unforgiven.
Angle dropped the title back to Austin on the October 8 episode of Raw when WWF Commissioner William Regal joined The Alliance and cost Angle the match. As part of the storyline, Angle subsequently turned heel again and joined The Alliance himself; during a WrestleMania X-Seven rematch between Vince McMahon and Shane McMahon, he interfered seemingly to aid Vince, but instead struck the members of team WWF with a steel chair. Angle later ultimately returned to the WWF side by enabling The Rock to defeat Austin in a "Winner Takes All" match between the WWF and The Alliance at Survivor Series. He remained a heel by claiming sole responsibility for the destruction of The Alliance.
At Vengeance, Angle lost to Steve Austin, who was the WWF Champion, as part of a one-night tournament to unify the WWF and WCW Heavyweight titles also involving Chris Jericho and The Rock. On January 20, 2002, Angle entered his first ever Royal Rumble match at the Royal Rumble, where he lasted until the final two before being eliminated by eventual winner Triple H. At No Way Out, Angle defeated Triple H, with assistance from special referee Stephanie McMahon, for the right to face the WWF Undisputed Champion at WrestleMania X8, but lost the title shot right back to him the next night on Raw. Angle briefly feuded with Kane, defeating him at WrestleMania X8. On the March 25 episode of Raw, Angle was drafted to the SmackDown! brand as part of the 2002 WWF draft lottery.
Angle then reignited his feud with Edge, defeating him at Backlash. The naturally balding Angle lost a "hair versus hair" match to Edge at Judgment Day, and his head was shaved bald. Angle once again lost to Edge in a steel cage match on the May 30 episode of SmackDown!, concluding their feud. After the match, Edge's tag partner Hulk Hogan attacked Angle and tried to strip of him of his wig, but Angle fled before he could do so. Angle later scored a submission victory over Hogan at King of the Ring, making him the first wrestler in WWE history to defeat Hogan via submission. During mid-2002, Angle routinely held open challenges on SmackDown!. Accepting one of these challenges, John Cena made his WWE televised debut on the June 27 taping of SmackDown!, losing to Angle after a roll-up pin. On the July 4 episode of SmackDown!, Angle faced WWE Undisputed Champion The Undertaker, which ended in controversial finish, with Angle locking Undertaker in a triangle choke, the referee counted Angle's shoulders down as the Undertaker tapped out. This confusion caused the match to be labeled a draw. At Vengeance, Angle received his rematch as he competed in a triple-threat match against Undertaker and The Rock for the championship, which he lost after being pinned by the Rock. Angle picked up a win against a newly debuted Rey Mysterio at SummerSlam.
In September, Angle started to feud with Chris Benoit, losing to him at Unforgiven. On the October 3 taping of SmackDown!, Angle and Benoit were teamed together by SmackDown! general manager Stephanie McMahon to compete in a tournament to determine the inaugural WWE Tag Team Champions. Angle became the fifth WWE Grand Slam Champion when he and Benoit won at No Mercy, defeating Edge and Rey Mysterio. Their team was successful, but problematic as the two bickered constantly, with Benoit often fed up with Angle's over-the-top antics. They made their first successful title defense by defeating Los Guerreros (Eddie Guerrero and Chavo Guerrero) at Rebellion. Their reign ended after they dropped the titles to Edge and Mysterio on the November 7 episode of SmackDown! in a two-out-of-three falls match. Angle and Benoit would receive another shot at the Tag Team Championship in a triple threat elimination match against Edge and Mysterio and Los Guerreros at Survivor Series, but failed after they were the first team eliminated; Los Guerreros eventually won.
Angle won his third WWE Championship at Armageddon, defeating Big Show with the help of Brock Lesnar. While still in his third reign, Angle began a new storyline when he gained the services of manager Paul Heyman and "Team Angle". Then -SmackDown! General manager Stephanie McMahon announced that Big Show would face Chris Benoit to determine who would face Angle for the title at the Royal Rumble. Benoit pinned Big Show to win the match. After the match Angle and Big Show brutally attacked Benoit. At the Royal Rumble, Angle defeated Benoit by forcing him to submit the ankle lock. He then began feuding with Brock Lesnar, who had won the 2003 Royal Rumble match, after he claimed to be the new top superstar on SmackDown!. Angle lost the WWE Championship in the main event of WrestleMania XIX to Lesnar, due to needing time off to recuperate from injuries. On April 11, 2003, Angle underwent neck surgery to repair nerve and spinal damage, calcium buildup, bone spurs, and intervertebral disc problems.
Angle returned as a face in June. Shortly after returning, Angle defeated Lesnar and Big Show in a triple threat match at Vengeance to regain the WWE Championship for the fourth time. During this time, Lesnar seemed to become an ally to Angle. Lesnar, however, secretly worked with Vince McMahon on a plot against Angle, turning on him during a steel cage match between himself and McMahon in which Angle was the special guest referee, and stated that he never tolerated losing the belt to him at Vengeance. After retaining the championship against Lesnar at SummerSlam by making him submit to the ankle lock, he dropped the title to Lesnar in an Iron Man match on the September 18 episode of SmackDown!. Angle then formed a five-man team to rival Lesnar's team at Survivor Series, with Angle's team coming out victorious, despite Angle being eliminated by Lesnar.
Angle then got involved in a feud with Eddie Guerrero. He was initially being a firm friend and ally to Eddie during the latter's feud with his nephew Chavo. At No Way Out, Guerrero defeated Lesnar to win the WWE Championship, while Angle defeated John Cena and Big Show in a triple threat match to become the number one contender for Guerrero's title at WrestleMania XX. On the following episode of SmackDown!, Angle attacked Guerrero, turning heel once again. After losing to Guerrero at WrestleMania, Angle began to once again suffer from legitimate neck problems and went in for surgery on his neck shortly after WrestleMania and was not scheduled to return to action for some time. He was made the on-screen General Manager of SmackDown!, with his absence from the ring attributed to injuries suffered after Big Show chokeslammed him off a ledge. Angle continued his feud with Guerrero throughout 2004. He cost Guerrero the WWE Championship against John "Bradshaw" Layfield in a Texas Bull Rope match at The Great American Bash by participating in the worked finish; Angle came down to the ring and showed a replay where JBL's shoulder hit the corner pad before Guerrero's hand. Angle was later fired by Vince McMahon as General Manager on the July 22, 2004 episode of SmackDown! after McMahon discovered that he was faking his handicapped status and put him in a match against Eddie Guerrero at SummerSlam. At SummerSlam, Angle defeated Guerrero by submission. On the September 9 episode of SmackDown!, Angle fought Guerrero in a lumberjack match that ended in a no contest when a brawl broke out. Big Show then made his return, attacking both Angle and Guerrero. This led to a match at No Mercy where Angle lost to Big Show.
On the November 4, 2004, episode of SmackDown!, during an unscripted segment of Tough Enough, Angle challenged the finalists to a squat thrust competition. Chris Nawrocki won the competition, and the prize Nawrocki won was a match against Angle. Angle quickly took Nawrocki down with a guillotine choke, but Nawrocki managed to make it to the ropes, forcing Angle to break the hold. Angle then took Nawrocki down with a double leg takedown, legitimely breaking his ribs. Angle then locked another guillotine choke on Nawrocki, pinning him in the process. After Angle defeated Nawrocki, Angle challenged the other finalists. Daniel Puder accepted Angle's challenge. Angle and Puder wrestled for position, with Angle taking Puder down, however, in the process, Puder locked Angle in a kimura lock. With Puder on his back and Angle's arm locked in the kimura, Angle pushed Puder's shoulders down, pinning him and one of two referees in the ring, Jim Korderas, quickly counted three to end the bout, despite the fact that Puder's shoulders were not fully down on the mat, bridging up at two.
At the Royal Rumble, after failing to win a triple threat match for the WWE Championship, involving Big Show and champion John "Bradshaw" Layfield, Angle later took part in the Royal Rumble match itself, but was eliminated in quick fashion by Shawn Michaels, causing Angle to return to the ring to eliminate Michaels in retaliation. After mocking Michaels by defeating his former tag team partner, Marty Jannetty, and attacking former manager, Sherri Martel, Angle defeated Michaels in an interpromotional match at WrestleMania 21. On the April 14 episode of SmackDown!, Angle defeated Eddie Guerrero as part of a tournament to determine the number one contender to the WWE Championship. In the same episode, Angle confronted fellow tournament entrant Booker T and his wife Sharmell after Sharmell predicted that Booker would win the tournament. On the April 21 episode of SmackDown!, Angle and John Bradshaw Layfield interfered in a tournament match between Booker and Big Show, rendering it a no-contest and thus creating a fatal four-way match against the remaining tournament entrants the next week, which Layfield won. At Judgment Day, Booker defeated Angle. On the June 2 episode of SmackDown!, Angle defeated Booker and Sharmell in a 2-on-1-handicap match after pinning Sharmell in a sexual position. Angle would again lose to Booker on the June 9 episode of SmackDown!, ending their feud. Angle appeared at ECW One Night Stand as an anti-ECW "crusader". At the end of ECW One Night Stand, Angle and other "crusaders" would engage in a brawl with ECW alumni led by Steve Austin, in which the crusaders were soundly beaten.
Angle resumed his feud with Michaels upon being drafted to the Raw brand in the 2005 WWE draft lottery, losing to Michaels at Vengeance. On the July 25, 2005 episode of Raw, Eugene took part in the "Kurt Angle Invitational" challenge. Angle was unable to make Eugene submit in the three-minute limit, winning his cherished Olympic gold medal (per match stipulation), and starting a feud between the two. The feud culminated at SummerSlam, where Angle defeated Eugene to regain his medal. Angle later feuded with John Cena for the WWE Championship. He challenged Cena at Unforgiven, but won by disqualification, therefore not winning the title. On the October 3 WWE Homecoming episode of Raw, he wrestled rival Shawn Michaels to a 2-2 draw in a 30-Minute Iron Man match, after which Michaels challenged him for a sudden death overtime, but Angle refused and walked out. He challenged Cena for the WWE Championship again in a triple threat match involving Michaels at Taboo Tuesday, but did not win, and then again lost to Cena at Survivor Series. Angle would continue his feud with Cena into 2006, defeating him in a non-title first blood match on the January 2 episode of Raw, after interference from Daivari. At New Year's Revolution, Angle again challenged Cena for the title, this time in an Elimination Chamber match, also involving Shawn Michaels, Kane, Carlito and Chris Masters. Angle would fail to win the match, as he was eliminated by Michaels. Angle wrestled his final match on Raw on January 16, in a losing effort to Shawn Michaels after Daivari inadvertently hit him with a steel chair while trying to target Michaels. Angle then attacked Daivari after the match, turning face in the process.
On the January 13 episode of SmackDown!, Angle returned to the SmackDown! brand as a surprise entrant in a twenty-man battle royal for the vacant World Heavyweight Championship. Angle won by last eliminating Mark Henry. He retained the title against Henry at the Royal Rumble. Shortly after the match, The Undertaker made his return and challenged Angle for the title. At No Way Out, Angle retained the title against Undertaker after a controversial finish where Angle pinned Taker while locked in a triangle choke. Undertaker challenged Angle to a rematch on the March 3 episode of SmackDown!, where Angle lost by disqualification after Mark Henry interfered and attacked Undertaker. This ensured that Angle would enter WrestleMania 22 as champion. Angle then began a three-way feud with Royal Rumble winner Rey Mysterio and Randy Orton (who defeated Mysterio at No Way Out to gain entrance to the SmackDown! main event at WrestleMania). At WrestleMania, Angle lost the title to Mysterio in the triple threat match after Mysterio pinned Orton.
On May 29, 2006, Angle was drafted to the newly created ECW brand. It was during this time that he acquired the nickname "The Wrestling Machine", wearing a mouth guard and quickly squashing opponents. Upon coming to ECW, he issued an open challenge for One Night Stand, which was accepted by Randy Orton. Angle defeated Orton at One Night Stand, later losing to him in a rematch at Vengeance. On the June 27 ECW taping, Angle challenged ECW World Heavyweight Champion Rob Van Dam to a title match, which he lost. Angle appeared sporadically on WWE television throughout mid-2006. On August 25, 2006, Angle was granted an early release from his WWE contract because of health reasons. Angle wrestled his last match at an ECW taping on August 8, which ended in a no-contest against Sabu.
On January 16, 2017, WWE announced that Angle would be inducted into the WWE Hall of Fame. On March 16, WWE revealed that his long-time rival John Cena would induct Angle at the Hall of Fame ceremony. On the April 3 episode of Raw after WrestleMania 33, Angle made his first WWE appearance in nearly 11 years after Mr. McMahon appointed Angle as the new general manager of Raw. On the May 29 episode of Raw, commentator Corey Graves informed Angle about some "scandalous information" that was sent to him about Angle, with Angle telling Graves "if this is true, it could ruin me". On the July 17 episode of Raw, Angle revealed that he had a son with a woman he dated in college. He stated that his son eventually ended up in the WWE. Angle then made the announcement that his (on-screen) son was Jason Jordan of American Alpha, thus moving Jordan to the Raw brand.
On October 20, WWE announced Angle's in-ring return after 11 years, replacing Roman Reigns due to medical issues and teaming with Dean Ambrose and Seth Rollins to face The Miz, Braun Strowman, Kane, Cesaro and Sheamus in a 5-on-3 handicap Tables, Ladders, and Chairs match at TLC: Tables, Ladders & Chairs. Angle (dressed in The Shield's ring attire), Ambrose, and Rollins won the match, despite Angle having initially been taken out when Braun Strowman executed a running powerslam through a table on Angle. On the October 30 episode of Raw, while addressing the fans, commissioner Stephanie McMahon confronted Angle, announcing that Angle would be the team captain of Team Raw at Survivor Series, adding that if Team Raw would lose, Angle would be fired. At the event, Angle's teammate Triple H attacked him, leading to his elimination by Shane McMahon, however, Team Raw still went on to win the match. At Elimination Chamber, Angle, along with Stephanie McMahon and Triple H, was present when Ronda Rousey signed her Raw contract, where Angle brought up the confrontation that Stephanie McMahon and Triple H had with Rousey and The Rock at WrestleMania 31 and that they both want to manipulate her. This caused Rousey to put Triple H through a table and be slapped by Stephanie McMahon before signing her contract. The following night on Raw, Angle claimed the allegations he made were false to keep his job before being attacked by Triple H. As a result, the following week, Angle scheduled himself to team with Rousey against Triple H and Stephanie McMahon in a mixed tag team match at WrestleMania 34, which Angle and Rousey won. Following WrestleMania, Angle found himself in a power struggle over the control of Raw, when the McMahon family appointed Baron Corbin as the constable of Monday nights on the June 4 episode of Raw. This continued until the August 20 episode of Raw, when Stephanie McMahon sent Angle on "vacation" before announcing that Baron Corbin would be acting general manager in Angle's absence.
On the October 8 episode of Raw, Angle made a surprise return, disguised under a mask as "The Conquistador", winning a battle royal after last eliminating Baron Corbin and qualifying for the WWE World Cup at Crown Jewel. At the event, Dolph Ziggler defeated Angle in the first round of the WWE World Cup Tournament. On November 5, Angle competed in his first match on Raw since 2006, for a spot in the Survivor Series tag match, losing to Drew McIntyre in dominating fashion, with McIntyre using Angle's own ankle lock finishing maneuver to make him submit. Angle returned at TLC on December 16 to help Braun Strowman, along with Apollo Crews, Finn Bálor, Bobby Roode, Chad Gable, and referee Heath Slater, beat Baron Corbin to strip him of authoritative power. The next night on Raw, Angle along with Crews, Roode and Gable, easily defeated Corbin in a handicapped-no disqualification match to prevent him from being the permanent general manager of Raw. At the 2019 Royal Rumble on January 27, 2019, Angle entered the match at number 4 but was eliminated by Shinsuke Nakamura.
In March, Angle announced he would retire at WrestleMania 35 and chose Baron Corbin as his final opponent at the event. During the following weeks, Angle faced several hand-picked wrestlers during his farewell tour, defeating Apollo Crews, Chad Gable, Samoa Joe and lost to AJ Styles via disqualification. In his final match, Angle lost to Corbin. On the Raw after WrestleMania, Angle attacked Corbin, and was subsequently attacked by a debuting Lars Sullivan. Afterwards, Angle transitioned to a backstage role as a producer.
On July 22, 2019, Angle appeared on the Raw Reunion episode and raised a toast alongside Triple H, Ric Flair, Hulk Hogan, Stone Cold Steve Austin and various other fellow wrestlers of his era. On the August 5 episode of Raw in his hometown of Pittsburgh, Angle made an appearance as the special guest referee for a match between Drew McIntyre and Cedric Alexander. However, McIntyre and Alexander took out each other before the match began and Angle was then attacked by "The Fiend" Bray Wyatt. On April 15, 2020, Angle was released from his WWE contract.
On May 27, Angle was the special guest referee in the Fight Pit match between Matt Riddle and Timothy Thatcher on the NXT brand. He appeared again two days later on the May 29 episode of SmackDown to announce the arrival of Matt Riddle to the brand.
On the June 27, 2022 episode of Raw, Angle made an appearance via a video message to congratulate John Cena on his career. Angle would appear on the August 29 episode of Raw, which took place in his hometown of Pittsburgh, sporting his old Team Angle attire. He would get into an altercation with Alpha Academy (Chad Gable and Otis) before being aided by The Street Profits (Angelo Dawkins and Montez Ford), which led to a tag team match between the two teams with the stipulation that if Alpha Academy won, Angle would have to join them. The Street Profits would win the match and afterwards, Angle celebrated with them by drinking milk. Later on in the night, Angle reunited with Edge and would get pranked by him with rigged pictures containing mocking slogans on the back of them in a similar fashion to a segment the duo had back in 2002.
Angle made his next appearance on the December 9 episode of SmackDown, where he celebrated his fifty-fourth birthday. He interacted with various superstars backstage including his storyline son, Jason Jordan, before once again getting into an altercation with Alpha Academy at the end of the show during his in-ring celebration; Angle would be aided by Gable Steveson, who drove a milk truck to the ring and the two sprayed Alpha Academy with milk from a hose, mimicking Angle's famous 2001 segment.