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Ric Flair
Ric Flair held the NWA/WCW World Heavyweight Championship a record 16 times across a career that stretched from the 1970s through the 2000s, a title reign count that remains the standard by which longevity and sustained relevance in professional wrestling's world championship picture is still measured. Flair's in-ring character, "The Nature Boy," built around a flamboyant, robe-and-limousine persona combined with a genuinely respected technical wrestling style, made him the dominant figure of the National Wrestling Alliance's territorial era before that promotion consolidated into the WCW that later competed directly with the WWF. His series of matches against rivals like Ricky Steamboat and Dusty Rhodes in the 1980s are still cited by wrestlers and historians as some of the finest in-ring performances the genre has produced, praised for pacing and psychology in an era when wrestling matches were often built around slower, more methodical storytelling than the faster style that came later. Flair's catchphrase "To be the man, you've got to beat the man" became one of wrestling's most quoted lines, and his influence carried into the next generation directly — his daughter Charlotte Flair became a dominant multi-time WWE women's champion in her own right, extending the Flair name's championship legacy into an entirely new era of the business.
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The Undertaker
The Undertaker's WrestleMania winning streak, "The Streak," ran undefeated for 21 consecutive years, from his debut WrestleMania VII win in 1991 through WrestleMania XXVII in 2011, making it one of the longest sustained undefeated runs at a single recurring event in the history of any competitive entertainment format. That streak finally ended at WrestleMania XXX in 2014, when Brock Lesnar defeated him in front of a shocked Superdome crowd in New Orleans — a result so unexpected that the arena reaction, largely stunned silence, became nearly as famous as the match itself, and remains one of the most talked-about singular moments in modern wrestling history. The Undertaker maintained his macabre, supernatural "Deadman" persona with remarkable consistency for nearly three decades, one of the longest-running unbroken characters in wrestling history, at a business where most performers' gimmicks are retooled or abandoned entirely well before that kind of longevity. His in-ring rivalries with performers across multiple eras — from Hulk Hogan-era legends through the Attitude Era and into the 2010s — gave him a career that bridged nearly every major period in WWE's modern history, and his 21-0 WrestleMania streak remains the singular achievement most associated with the entire event's identity.
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