Henry joined the Nation of Domination faction with Farooq, The Rock, The Godfather and D'Lo Brown on January 12, 1998, becoming a villain in the process. After The Rock usurped Farooq's position as leader, Henry switched loyalties to The Rock. He also competed at WrestleMania XIV in a tag team battle royal, with Brown as his partner, but they did not win. After the Nation disbanded, he engaged in a short feud with The Rock, defeating him at Judgment Day: In Your House with help from Brown, and then forming a permanent team with Brown, gaining Ivory as a manager. During the next year, Henry gave himself the nickname "Sexual Chocolate", and was involved in controversial angles with Chyna and a transvestite. During a match at the August 1999 pay-per-view, SummerSlam, between Brown and Jeff Jarrett for the WWF Intercontinental and WWF European Championships (both held at the time by Brown), Henry turned on Brown and helped Jarrett win the match and the titles. The next night, Henry was awarded the European title by Jarrett in return for his help. Henry dropped the title one month later to Brown at the Unforgiven pay-per-view.
After this, Henry turned into a fan favorite, and was seen on television romancing WWF women from Chyna to Mae Young as part of the "Sexual Chocolate" gimmick. He feuded with Viscera during this time as part of a storyline where Viscera splashed Mae Young while she was carrying Henry's child. Young would go on to give birth to a hand. Along with this, Henry was made part of various other embarrassing and infamous storylines, including the admission that he was a sex addict.
In 2000, Henry was sent to Ohio Valley Wrestling (OVW) to improve his conditioning and skills. In OVW, Henry teamed with Nick Dinsmore to compete in a tournament for the OVW Southern Tag Team Championship in mid-2001. Later that year, he went on hiatus from wrestling to concentrate on weightlifting, and on February 23, 2002, he won a strongman competition, during the Arnold Classic in Columbus, Ohio, claiming a $75,000 Humvee as his prize.
Henry returned to the WWF the next month and was sent to the SmackDown! brand, where he developed an in-ring persona of performing "tests of strength" while other wrestlers took bets on the tests, but the gimmick met with little success. During this time he competed against such superstars as Chris Jericho and Christian. After being used sporadically on WWE (formerly WWF) television during 2002, as he was training for a weightlifting contest, and suffering a knee injury, Henry was sent back to OVW for more training.
In August 2003, Henry returned to WWE television on the Raw roster, where he found some success as a member of "Thuggin' And Buggin' Enterprises," a group of African Americans led by Theodore Long who worked a race angle in which they felt they were victims of racism and were being held down by the "white man". During that time, Henry was involved in a brief program with World Heavyweight Champion Goldberg when former champion, Triple H, put a bounty on Goldberg. This was followed by a brief rivalry with Shawn Michaels, before he engaged in a scripted rivalry with Booker T. After defeating Booker T twice, once in a street fight and once in a six-man tag team match, he lost to Booker T at the Armageddon pay-per-view in December 2003. At a practice session in OVW in February 2004, Henry tore his quadriceps muscle, and was out for over a year after undergoing surgery. Henry was then utilized by WWE as a public relations figure during his recovery, before returning to OVW to finish out 2005.
During the December 30 episode of SmackDown!, Henry made his return to television, as he interfered in a WWE Tag Team Championship match, joining with MNM (Joey Mercury, Johnny Nitro, and Melina), to help them defeat Rey Mysterio and Batista for the championship. A week later on SmackDown!, Henry got in a confrontation with the World Heavyweight Champion, Batista, and went on to interfere in a steel cage match between MNM and the team of Mysterio and Batista, helping MNM to retain their titles. Henry then had another match with Batista at a live event where Batista received a severely torn triceps that required surgery, forcing him to vacate his title. On the January 10, 2006 episode of SmackDown!, Henry was involved in a battle royal for the vacant World Heavyweight Championship. He was finally tossed out by Kurt Angle, who won the title.A week later, Henry received assistance from Daivari, who turned on Angle and announced that he was the manager of Henry. With Daivari at his side, Henry would face Kurt Angle for the World Heavyweight title at the 2006 Royal Rumble in January, which he lost when Angle hit him with a chair (without the referee seeing) and pinned Henry with a roll-up.On the March 10 episode of SmackDown!, after putting Kurt Angle through a table with a diving splash, Henry was then challenged to a casket match by The Undertaker at WrestleMania 22. Henry vowed to defeat The Undertaker and end his streak at WrestleMania, but was unsuccessful in this quest as The Undertaker would defeat Henry at the event. Henry would get a rematch against the Undertaker on the April 7 episode of SmackDown!, however it ended in a no contest when Daivari announced his new client, The Great Khali, who was also making his debut. Khali then went to the ring and started to attack the Undertaker, thus ending the feud between them.During the rest of April and May, Henry gained a pinfall victory over the World Heavyweight Champion, Rey Mysterio in a non-title match. Henry would also enter the King of the Ring tournament, in which he was defeated by Bobby Lashley in the first round. He later cost Kurt Angle his World Heavyweight Championship opportunity against Mysterio, when he jumped off the top rope and crushed Angle through a table. Henry was then challenged by Angle to face off at Judgment Day, Henry then sent a "message" to Angle by defeating Paul Burchill. At Judgment Day, Henry defeated Angle by countout. Although winning, Angle got his revenge after the match by hitting Henry with a chair and putting him through a table.Henry later went on what was referred to as a "path of destruction", causing injuries to numerous superstars. Henry "took out" Chris Benoit and Paul Burchill on this path of destruction, and attacked Rey Mysterio and Chavo Guerrero. These events led up to a feud with the returning Batista, whom Henry had put out of action with a legitimate injury several months beforehand. When Batista returned he and Henry were scheduled to face one another at The Great American Bash in July. Weeks before that event, however, on the July 15, 2006 edition of Saturday Night's Main Event, Henry was involved in a six-man tag team match with King Booker and Finlay against Batista, Rey Mysterio, and Bobby Lashley. During the match, Henry was injured, canceling the scheduled match at The Great American Bash, as Henry needed surgery. Doctors later found that Henry completely tore his patella tendon off the bone and split his patella completely in two.Henry returned on the May 11, 2007 episode of SmackDown!, after weeks of vignettes hyping his return. He attacked The Undertaker after a World Heavyweight Championship steel cage match with Batista, allowing Edge to take advantage of the situation and use his Money in the Bank contract. Henry then began a short feud with Kane, defeating him in a Lumberjack Match at One Night Stand. Shortly after, Henry made an open challenge to the SmackDown! locker room, which nobody ever accepted. In the coming weeks he faced various jobbers—wrestlers who consistently lose to make their opponents look stronger—and quickly defeated them all. On August 3, he claimed that nobody accepted the open challenge to step into the ring with him because of what he had done to The Undertaker, presenting footage of his assault on the Undertaker. The Undertaker responded over the following weeks, playing various mind games with Henry.Henry finally faced The Undertaker again at Unforgiven in September, losing to him after being given a Last Ride. Two weeks later, Henry lost a rematch to The Undertaker after The Undertaker performed a chokeslam on Henry.After a short hiatus, Henry returned to WWE programming on the October 23 episode of ECW, attacking Kane, along with The Great Khali and Big Daddy V. Henry then began teaming with Big Daddy V against Kane and CM Punk, and was briefly managed by Big Daddy V's manager, Matt Striker. At Armageddon, Henry and Big Daddy V defeated Kane and Punk.Before WrestleMania XXIV aired, Henry participated in a 24-man battle royal to determine the number one contender for the ECW Championship, but failed to win.As part of the 2008 WWE Supplemental Draft, Henry was drafted to the ECW brand. At Night of Champions, Henry defeated Kane and Big Show in a Triple Threat match to capture the ECW Championship in his debut match as an ECW superstar. Upon winning the title, it was made exclusive to the ECW brand once again. Henry's title win came nearly a full decade after he was awarded the European Championship, which was back in 1999 and the last title he held in the WWE. A few weeks later, Hall of Famer Tony Atlas returned to WWE to act as Henry's manager. A month after Henry's title win, ECW General Manager, Theodore Long, unveiled a new, entirely platinum ECW Championship belt design. Henry would lose the title at Unforgiven in the Championship Scramble match to Matt Hardy.Henry attempted to regain the championship throughout the end of 2008, including a match against Hardy at No Mercy, but was unsuccessful. Henry and Atlas then engaged in a scripted rivalry against Finlay and Hornswoggle, which included Henry losing a Belfast Brawl at Armageddon. At the start of 2009, Henry qualified for the Money in the Bank ladder match at WrestleMania XXV, and was involved in a series of matches with the other competitors on Raw, SmackDown, and ECW. He was unsuccessful at WrestleMania, however, as CM Punk won the match. In May, Henry began a scripted rivalry with Evan Bourne, which began after Bourne defeated Henry by countout on the May 26 episode of ECW.On June 29, Henry was traded to the Raw brand, and made his redebut for the brand that night as the third opponent in a three-on-one gauntlet match against Randy Orton, which he won, turning Henry into a fan favorite in the process. In August 2009, Henry formed a tag team with Montel Vontavious Porter, and the two challenged the Unified WWE Tag Team Champions Chris Jericho and The Big Show at Breaking Point, but were unsuccessful.