In the 1990s, Diamond Dallas Page (DDP) was initially portrayed as an arrogant and wealthy individual who flaunted his lavish lifestyle. He engaged in a feud with Johnny B. Badd (Marc Mero) centered around the Television title, their contrasting personalities, and Badd's romantic involvement with DDP's valet, Kimberly. Throughout the feud, DDP found himself on the losing end of most matches.

Following the rivalry with Badd, DDP began a slow transition away from his obnoxious persona while feuding with Eddie Guerrero over the non-prestigious, non-title, ring from the Lord of the Ring Tournament. Around this time, the WCW vs. nWo storyline started making significant waves in the wrestling world. During the tournament for the vacant United States Heavyweight Championship, DDP received assistance from Kevin Nash and Scott Hall, who felt unappreciated. However, in the tournament final, Hall and Nash turned on Page, attacking him and ultimately helping Eddie Guerrero secure the victory. Subsequently, Hall and Nash approached Page, attempting to recruit him into the nWo. To their surprise, Page responded by delivering Diamond Cutters, marking the beginning of his transformation into a fan-favorite and igniting a heated feud with the nWo.

DDP, often referred to as the People's Champion during this time, became one of the main adversaries of the nWo. While his initial issues were with the Outsiders (Hall and Nash), his feud with the nWo gained prominence when he faced Macho Man Randy Savage in the main events of Spring Stampede and Great American Bash 1997. Their rivalry reached its climax at Halloween Havoc 1997 with Savage defeating Page in a Las Vegas sudden-death match.

At Starrcade 1997, Page captured the United States Heavyweight Championship from nWo member Curt Hennig. As champion, he engaged in feuds with Chris Benoit and Raven before eventually losing the title to Raven.

DDP faced Goldberg for the WCW Heavyweight Championship in the main event of Halloween Havoc. Although he didn't emerge victorious, he became involved in a back-and-forth feud for the United States Championship with Bret Hart. At Spring Stampede 1999, DDP won the WCW Heavyweight Championship in a four-way match that also included Hollywood Hogan, Sting, and Ric Flair.

Following his championship victory, DDP adopted a more villainous persona and began a rivalry with Kevin Nash. He eventually lost the title to Nash at Slamboree 1999. Subsequently, Page aligned himself with Bam Bam Bigelow and Chris Kanyon, forming a group known as The Jersey Triad, and focused on pursuing the WCW World Tag Team Championships.

DDP continued with WCW until the company's closure. He was one of the prominent WCW wrestlers to participate in the WWF invasion in 2001. DDP made his debut in the World Wrestling Federation on the June 18, 2001, episode of Raw, revealing himself as the stalker of The Undertaker's wife, Sara. He faced The Undertaker at King of the Ring 2001 but was defeated in a confrontation. DDP represented the Alliance in the Team WWF vs. Team WCW/ECW Inaugural Brawl at the Invasion pay-per-view, which marked his only main event with the WWF. Shortly afterward, DDP suffered a loss to Sara in a match on the August 20th episode of Raw.

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