Kurt Angle joined WWE in 1999, and he had a lot of pressure on him to do well as he was one of the biggest acquisitions in WWE history. Angle certainly delivered on his potential, and he had one of the best debut years in 2000. Angle captured the WWE Championship, Intercontinental Title, European Championship and was crowned King of the Ring.
Moreover, Angle is a six-time World Champion overall in WWE, and he is a Grand Slam Champion. Whilst, Angle's career was filled with many memorable moments, his career did have some illogical moments which left fans scratching their heads.
10 Main Eventing Royal Rumble 2006
Traditionally the Royal Rumble match closes out a Royal Rumble pay-per-view as it's the match that fans eagerly anticipate all year. However, for the first time in eight years at Royal Rumble 2006, a World Title match closed out the show.
Kurt Angle is a big draw, and he defended the World Heavyweight Championship against Mark Henry. Angle retained the gold but they only closed out the show, for Undertaker to return and challenge Angle at No Way Out and for the ring to come apart. The Royal Rumble match or Cena dethroning Edge for the WWE Title should have gone on last.
9 Joining The Alliance
"The Old Stone Cold" returned at Invasion 2001 when Austin turned his back on the WWE and joined The Alliance. However, that led to Kurt Angle becoming one of the top babyfaces in the company, and he naturally chased after Steve Austin's WWE Championship.
Angle was doing an exceptional job as a babyface but old habits die hard and Angle turned heel once more by joining The Alliance. It made little sense for Angle to join The Alliance but at Survivor Series 2001, he turned his back on The Alliance and re-joined Team WWE aiding them to victory.
8 Stalking Sharmell
In 2005, two former World Champions in Kurt Angle and Booker T feuded which had the prospect of becoming a legendary rivalry. Unfortunately, one of the worst storylines in Angle's career was that he was obsessed with wanting to have sex with Booker T's wife Sharmell.
Angle was uncomfortable doing this storyline in reality but being a team player Angle just got on with it. This storyline certainly would not fly today, and it was dropped as Angle went on to do bigger and better things by getting drafted to Raw.
7 Moving To ECW
Days into 2006, Kurt Angle returned to SmackDown and captured the World Heavyweight Championship. He tore the house down with Undertaker at No Way Out and walked into WrestleMania 22 as champion. Things were going smoothly for Angle but they soon went downhill when he got drafted to ECW in the summer.
Angle wasn't the only big name to jump ship as fellow former World Champion Big Show moved to ECW with better success. The Olympic Gold Medalist wasn't best pleased by getting drafted to ECW which led to his departure.
6 Winning The WCW Championship
After the fallout of Invasion, Kurt Angle was on a rampage and wanted to inflict pain on Stone Cold Steve Austin and The Alliance. On the July 26, 2001, edition of SmackDown, Angle challenged Booker T for the WCW Championship.
They had a decent match but with Booker freshly join WWE, he needed to get a big win under his belt. That failed to materialize, and Angle defeated him for his lone WCW Championship reign. Whilst it was a significant moment in Angle's career, he only held the gold for 4 days as Booker regained the gold on the following episode of Raw which made the title switch pointless in the first place.
5 Failing To Beat John Cena For The WWE Title
A switch flicked in Kurt Angle's mind in 2005, and The Olympic Gold Medalist was untouchable at times with the performances that he put on in the ring. Angle relished a new challenge by leaving SmackDown and plying his trade on the Raw brand. After a lackluster feud with Eugene, Angle became John Cena's next challenger for the WWE Championship.
Cena and Angle's rivalry is overlooked, and Angle is one of the best rivals in Cena's career. They squared off at Unforgiven with Angle prevailing by DQ, and Shawn Michaels was adding to the mix in a competitive triple threat match at Taboo Tuesday. Their feud culminated at Survivor Series with Cena retaining but Angle certainly deserved another WWE Title run.
4 Not Winning A Royal Rumble Match
Kurt Angle is often in the conversation for being one of the greatest competitors to lace up a pair of boots. However, missing from his impressive resume is a Royal Rumble triumph which is quite surprising considering that Angle has featured in many main events.
The closest Angle came to achieving that feat was a runner-up finish in 2002 losing out to the returning Triple H. Nevertheless, he's had some good memories at the Rumble as he retained the WWE Title against The Game and Chris Benoit respectively in 2001 and 2003.
3 Retirement Match Against Baron Corbin
Kurt Angle's in-ring career was coming to an end at WrestleMania 35 but not the way Angle wanted it to end. The former six-time WWE World Champion's retirement match was against Baron Corbin. Corbin's a decent in-ring performer but Angle certainly deserved to ride into the sunset against a marquee name.
Fans were disinterested in the match as they had witnessed Triple H send Batista into retirement in an exceptional match. Nevertheless, Angle was no longer operating at the peak of his powers with injuries mounting up and Corbin was victorious in this forgettable contest.
2 Joining The Shield At TLC 2017
TLC 2017 marked Kurt Angle's in-ring return in a WWE ring for the first time in 11 years. However, it wasn't in the circumstances that Angle would have imagined as he replaced Roman Reigns as an honorary member of The Shield. He teamed up with Seth Rollins and Dean Ambrose to face off with Kane, Braun Strowman, The Miz, Cesaro, and Sheamus in a three-on-two TLC handicap match.
There's no doubt that Angle looked rusty but he put on a decent performance. Angle didn't need to compete in this match as a member of The Shield as he simply could not keep up with the pace in this contest.
1 Not Winning The WWE Championship From Steve Austin At SummerSlam 2001
Kurt Angle finally got his hands on Stone Cold Steve Austin in an outstanding WWE Championship match at SummerSlam 2001. Angle bled profusely but he had a refusal to quit as he kicked out of several Stone Cold Stunners.
With Austin being a heel, he would cheat to hold onto his title by any means necessary. It was heartbreak for Angle as Austin got himself intentionally disqualified to retain the title. Angle did go on to beat Austin for the WWE Championship at Unforgiven in front of his hometown fans but winning at SummerSlam would have been a big deal with SummerSlam being a massive pay-per-view.