Holyfield started out professionally as a light heavyweight with a televised win in six rounds over Lionel Byarm at Madison Square Garden on November 15, 1984. On January 20, 1985 he won another six-round decision over Eric Winbush in Atlantic City, New Jersey. On March 13, he knocked out Fred Brown in the first round in Norfolk, Virginia, and on April 20, he knocked out Mark Rivera in two rounds in Corpus Christi, Texas. Both he and his next opponent, Tyrone Booze, moved up to the cruiserweight division for their fight on July 20, 1985 in Norfolk, Virginia. Holyfield won an eight-round decision over Booze. Evander went on to knock out Rick Myers in the first round on August 29 in Holyfield's hometown of Atlanta. On October 30 in Atlantic City he knocked out opponent Jeff Meachem in five rounds, and his last fight for 1985 was against Anthony Davis on December 21 in Virginia Beach, Virginia. He won by knocking out Davis in the fourth round. He began 1986 with a knockout in three rounds over former world cruiserweight challenger Chisanda Mutti, and proceeded to beat Jessy Shelby and Terry Mims before being given a world title try by the WBA's world cruiserweight champion Dwight Muhammad Qawi. In what was called by The Ring as the best cruiserweight bout of the 1980s, Holyfield became world champion by defeating Qawi by a narrow 15 round split decision. He culminated 1986 with a trip to Paris, France, where he beat Mike Brothers by a knockout in three, in a non-title bout. In 1987, he defended his title against former Olympic teammate and Gold medal winner Henry Tillman, who had beaten Mike Tyson twice as an amateur. He retained his belt, winning by seventh round knockout, and then went on to unify his WBA belt with the IBF belt held by Ricky Parkey, knocking Parkey out in three rounds. For his next bout, he returned to France, where he retained the title with an eleven round knockout against former world champion Ossie Ocasio. In his last fight of '87, he offered Muhammad Qawi a rematch, and this time, he beat Qawi by a knockout in four. 1988 was another productive year for Holyfield; he started by becoming the first universally recognized world cruiserweight champion after defeating the WBC's defending world champion Carlos De León at the Las Vegas. The fight was stopped after eight rounds.
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After that fight, he announced he was moving up in weight to pursue the world heavyweight crown held by Tyson. His first fight as a Heavyweight took place on July 16, when he beat former Tyson rival James "Quick" Tillis by a knockout in five, in Lake Tahoe, Nevada (Tillis had gone the distance with Tyson). For his third and final bout of '88, he beat former world heavyweight champion Pinklon Thomas, also by knockout, in seven rounds. Holyfield began 1989 meeting another former world heavyweight champion, Michael Dokes. This fight would also be named one of the best fights of the 1980s by Ring magazine, as best heavyweight bout of the 1980s. Holyfield won by a knockout in the tenth round, and then he met Brazilian champion Adilson Rodrigues, who lasted two rounds. His last fight of the 1980s was against Alex Stewart, a hard punching fringe contender. Stewart shocked Holyfield early, with quick, hard punches, but eventually fell in eight. In 1990, Holyfield beat Seamus McDonagh, knocking him out in four rounds. By this time, Holyfield had been Ring Magazine's Number 1 contender for two years and had yet to receive a shot at Tyson's heavyweight title. Holyfield had been promised a title shot against Tyson in 1990. Before that fight could occur, in what many consider to be the biggest upset in boxing history, relatively unknown boxer, 29-year old, 231 lb. James "Buster" Douglas defeated the 23-year old, 218 lb. Mike Tyson in ten rounds in Tokyo to become the new undisputed heavyweight champion. Instead of fighting Tyson, Holyfield would be Douglas' first title defense. They met on October 25, 1990. Douglas came into the fight at 246 lb. and offered little in the fight against Holyfield, who was in great shape at 208 lb. In the third round Douglas tried to start a combination with a big right uppercut. Holyfield countered with a straight right hand that was lightning quick, and Douglas went down for the count. Holyfield was the new undefeated, undisputed heavyweight champion of the world. At the time of the knockout, Holyfield was ahead on all three judges' scorecards, all seeing it 20–18 for Holyfield. In his first defense, he beat former and future world champion George Foreman by unanimous decision in 12. The fight was billed as a "Battle for the Ages", a reference to the age differential between the young undefeated champion (28 years old), and the much older George Foreman (42 years old). Holyfield weighed in at 208 pounds and Foreman weighed in at 257 pounds. Foreman lost the fight by a unanimous decision, but surprised many by lasting the whole 12 rounds against a much younger opponent, even staggering Holyfield a few times and knocking him off balance in the seventh round.
Then a deal was signed for him to defend his crown against Mike Tyson in November 1991. Tyson delayed the fight, claiming he was injured in training, but was then convicted for the rape of Desiree Washington and sentenced to six years in prison, so the fight did not happen at that time. They would fight in 1996 (Holyfield won by a TKO in 11) and a rematch in 1997 (Holyfield won by disqualification in 3, after Tyson bit both of his ears). Holyfield made his next defense in Atlanta against Bert Cooper, who surprised him with a very good effort. Holyfield scored the first knockdown of the fight against Cooper with a powerful shot to the body, but Cooper returned the favor with a good right hand that sent Holyfield against the ropes; while not an actual knockdown, referee Mills Lane gave Holyfield a standing 8-count. Having suffered the first technical knockdown of his professional career, Holyfield regained his composure quickly and administered a beating that left Cooper still on his feet, but unable to defend himself. Holyfield landed brutal power shots, culminated by repeated vicious uppercuts that would snap Cooper's head back. Referee Mills Lane stopped the bout in the seventh. In his first fight of 1992, he faced former world heavyweight champion Larry Holmes, who was 42 years old, and had just pulled off an upset against Ray Mercer. During the bout, Holyfield suffered the first scar of his career with a gash opening up over his eye, the result of Holmes' elbow.The fight ended with a unanimous decision in favor of Holyfield. In the beginning of a trilogy of bouts with the 25-year old Riddick Bowe, who had won a silver medal in the 1988 Olympics, in the Super Heavyweight division, he suffered his first defeat when Bowe won the undisputed title by a 12-round unanimous decision in Las Vegas. Round Ten of that bout was named the Round of the Year by Ring Magazine. Holyfield was knocked down in round 11. He made the mistake of getting into a slugfest with the younger, bigger and stronger Bowe, leading to his defeat. He began 1993 by beating Alex Stewart in a rematch, but this time over the 12-round unanimous distance.
Then came the rematch with Bowe on November 6, 1993. In what is considered by many sporting historians as one of the most bizarre moments in boxing's history, during round seven the crowd got off their feet and many people started to run for cover and yell. Holyfield took his eyes off Bowe for one moment and then told Bowe to look up to the skies. What they saw was a man in a parachute flying dangerously close to them. The man almost entered the ring, but his parachute had gotten entangled in the lights, and he landed on the ropes and apron of the ring, and he was then pulled into the crowd, where he was beaten by members of Bowe's entourage. Bowe's pregnant wife, Judy, fainted and had to be taken to the hospital from the arena. Twenty minutes later, calm was restored and Holyfield went on to recover his world heavyweight titles with a close 12 round majority decision. The man who parachuted down to the middle of the ring became known as The Fan Man and the fight itself became known as the Fan Man Fight. His victory over Bowe that year helped Holyfield being named as ABC's Wide World of Sports Athlete of the Year for 1993. His next fight, April 1994, he met former WBO light heavyweight and heavyweight champion of the world Michael Moorer, who was attempting to become the first southpaw to become the universally recognised world heavyweight champion. He dropped Moorer in round two, but lost a twelve round majority decision. When he went to the hospital to have his shoulder checked, he was diagnosed with a heart condition, and had to announce his retirement from boxing. It would later surface that the chairman of the medical advisory board for the Nevada State Athletic Commission believed his condition to be consistent with HGH use. However, watching a television show hosted by preacher Benny Hinn, Holyfield says he felt his heart heal. He and Hinn subsequently became friends, and he became a frequent visitor to Hinn's crusades. In fact, during this time, Holyfield went to a Benny Hinn crusade in Philadelphia, had Hinn lay hands on him, and gave Hinn a check for $265,000 after he was told he was healed. He then passed his next examination by the boxing commission. Holyfield would later state that his heart was misdiagnosed due to the morphine pumped into his body.In 1995, Holyfield returned to the ring with a ten round decision win versus former Olympic gold medalist, Ray Mercer. He was the first man to knock down Mercer. Holyfield and Bowe then had their rubber match. Holyfield knocked Bowe down with a single left hook but Bowe prevailed, by a knockout in eight. Holyfield would later claim that he contracted Hepatitis A before the fight.
1996 was a very good year for Holyfield. First, he met former world champion Bobby Czyz, beating him by a knockout in six. Then, he and Mike Tyson finally met. Tyson had recovered the WBC's and the WBA's world heavyweight championship and, after being stripped of the WBC title for not facing Lennox Lewis, defended the WBA title against Holyfield on November 9 of that year. Tyson was heavily favored to win, but Holyfield made history by defeating Tyson in an 11th round TKO. This was the third occasion on which Holyfield won the WBA heavyweight title—however, the fight was not recognised as being for the linear heavyweight championship, which was held by George Foreman at the time. Muhammad Ali remains the only heavyweight champion to hold the linear championship three times. Holyfield's rematch with Tyson took place on June 28, 1997. Known as "The Bite Fight," it would go into the annals of boxing as one of the most bizarre fights in history. The infamous incident occurred in the third round, when Tyson bit Holyfield on one of his ears and had two points deducted. Referee Mills Lane decided to disqualify Tyson initially, but after Holyfield and the ringside doctor intervened and said Holyfield could continue, he relented and allowed the fight to go on. However, Tyson went on to bite Holyfield again, this time on the other ear. Tyson, with his teeth, tore off the top of his ear, known as the helix, and spit the flesh out on the ring. The immediate aftermath of the incident was greeted by instant bedlam. Tyson was disqualified and a melee ensued. Tyson claimed his bites were a retaliation to Holyfield's unchecked headbutts, which had cut him in both fights. Others argued that Tyson, knowing he was on his way to another knockout loss, was looking for a way out of the fight. His former trainer, Teddy Atlas, had predicted that Tyson would get himself disqualified, calling Tyson "a very weak and flawed person."
On October 13, 2007, Holyfield was defeated by Sultan Ibragimov. Although unable to defy his critics by winning a fifth heavyweight title, Holyfield refused to be backed up by the young champion and even rattled him in the closing part of the 12th round. The fight was mostly uneventful, however, with neither fighter being truly staggered or knocked down. In most exchanges, Sultan was able to land two punches to Holyfield's one. The end result was a unanimous decision for Ibragimov, with scores of 118–110, and 117–111 twice. He told BBC Scotland's Sports Weekly "I'm gonna fight, be the heavyweight champion of the world one more time. Then I'm gonna write another book and tell everybody how I did it." On December 20, 2008 he fought, at the Hallenstadion in Zürich Switzerland, the WBA heavyweight champion Nikolai Valuev for a paycheck of $600,000, the lowest amount he has ever received for a championship fight. At the weigh-in, he weighed 214 pounds, Valuev weighed a career low of 310 pounds. Valuev defeated Holyfield by a highly controversial majority decision after a relatively uneventful bout. One judge scored the bout a draw 114–114, while the others had Valuev winning 116–112 and 115–114. Many analysts were outraged at the decision, thinking Holyfield had clearly won. There was talk of a rematch in 2009. The WBA did their own investigation into the controversial decision; "As the World Boxing Association (WBA) always cares about and respects the fans' and the media's opinion, the Championship Committee has ordered a panel of judges to review the tape of the fight between Nikolai Valuev and Evander Holyfield, for the WBA heavyweight title", read a statement from the WBA. The organization also expressed that they "will give a decision accordingly in the following weeks." Many speculated that an immediate rematch would be the most likely scenario, but this never materialised. Valuev lost the WBA title in his next fight against British boxer David Haye.
Holyfield is the younger brother of actor and dancer, Bernard Holyfield, and currently lives and trains in Fayette County, Georgia with his third wife Candi and their two children; he has at least eleven children. By 1992, Holyfield was already a household name, announcing multiple products on television, such as Coca Cola and Diet Coke. He also had a video game released for the Sega Genesis and the Sega Game Gear: Evander Holyfield's Real Deal Boxing. After his conversion, he started professing his Christianity everywhere, reminding the public before and after his fights that he is a born-again Christian. In 1996 Holyfield was given the opportunity to carry the Olympic torch when it was on its way to his hometown of Atlanta for that year's Olympics. October 4 of this year he was married to Dr. Janice Itson, with whom he had one child. He founded Real Deal Records which signed the briefly successful group Exhale. On September 22, 2007 Holyfield released the Real Deal Grill cooking appliance via TV infomercials. The Real Deal Grill is manufactured by Cirtran Corp. Holyfield's popularity has led to numerous television appearances for the boxer. His first television show appearance was the Christmas special of the Fresh Prince of Bel-Air in 1990, playing himself. In 2005, Holyfield came in fifth place on ABC's Dancing with the Stars with his partner Edyta Sliwinska. He also made an appearance on the original BBC Strictly Come Dancing "Champion of Champions" showdown, which featured the final four teams from the 2005 edition of the British series, plus two celebrities from spinoff versions, paired with British professional dancers, one featuring Holyfield paired with Karen Hardy, and Rachel Hunter paired with Brendan Cole. Holyfield also had minor roles in three movies during the 1990s, Summer of Sam, Necessary Roughness, and Blood Salvage (which he also produced). He made a guest appearance on Nickelodeon's Nickelodeon GUTS during its third season in 1994. He appeared once in an episode of Phineas and Ferb. In the episode he is an animated character but the producers wanted to make the most of Holyfield's ear, so his animated character was only given half an ear. On August 13, 2007, Holyfield was confirmed to participate in a boxing match at World Wrestling Entertainment's Saturday Night's Main Event against Matt Hardy. He replaced Montel Vontavious Porter, who had to pull out after being legitimately diagnosed with a heart condition that was not part of a storyline. In late 2007 and early 2008, Holyfield was among a number of celebrities to be doing television ads for the restaurant chain Zaxby's. In June 2008 a legal notice was placed by Washington Mutual Bank stating that Holyfield's $10 million, 54,000-square-foot (5,000 m2), 109 room, 17 bathroom suburban Atlanta estate would be auctioned off on July 1, 2008 due to foreclosure. Adding to his financial problems, Toi Irvin, mother of his 10 year old son, filed suit for non-payment of two months child support (he pays $3,000 per month for this child). A Utah landscaping firm also has gone to court seeking $550,000 in unpaid debt for services.