Early years (1983-1992)

Matthews was born in Codsall Wood, Staffordshire, England, before moving with his family to London. Matthews made his ring debut wrestling in carnivals and on the North Pier of Blackpool at the age of fifteen. He wrestled professionally all over England, where he regularly teamed with Robbie Brookside, before going to the United States in 1992. He wrestled his first few matches under the name Roy Regal before settling on the name Steve Regal, a name he saw in an American wrestling magazine (in use by "Mr. Electricity" Steve Regal). Both Regal and Brookside appeared on World of Sport in several matches that were televised.

World Championship Wrestling (1992—1998)

Matthews started in World Championship Wrestling (WCW) as Steve Regal, beginning as a face character. He became the villain Lord Steven Regal in 1992, claiming descent from William the Conqueror. At times arrogantly charming in this persona, one of his memorable statements to a post-match interviewer was, "Do you know what my New Year's resolution is going to be? To wake up a half an hour earlier so I can hate you more."

Bill Dundee served as his manager under the name Sir William, and he won the World Television Championship four times. He teamed up with fellow aristocrat Jean-Paul Levesque, but after Levesque left WCW, he was replaced by Alabama-born Bobby Eaton. Regal formed the team The Blue Bloods and was involved in humorous vignettes where he tried to teach Eaton the finer points of dining and the proper usage of the Queen's English. He renamed him "Earl" Robert Eaton and soon added "Squire" David Taylor to the team. They came close to winning the WCW Tag Team Titles, but never did.

During his stint in WCW, Regal faced Antonio Inoki at Clash of the Champions on August 28, 1994. Regal also had a match with Shinya Hashimoto for the IWGP Heavyweight Championship. On February 9, 1998, Regal had a match with Bill Goldberg on Monday Nitro, in which he appeared more aggressive and stiff than expected with the then-rising star. It was later revealed that most of Regal's moves on Goldberg were shoot-style moves, which caught Goldberg off-guard at the time. It was rumored that WCW management was upset with Regal because, even though he did job to Goldberg as expected, he was supposed to lose to Goldberg in a squash, like most of Goldberg's other competitors at the time, as opposed to actually keeping the match competitive. However, in his autobiography, Regal disputes this.

World Wrestling Federation (1998—1999)

Regal's initial appearance in the World Wrestling Federation was on the June 29, 1998 edition of Raw Is War, in which he defeated Droz via submission with the Regal Stretch. Regal was not seen on WWF television again until he returned that fall with a "Real Man's Man" builder/lumberjack style looking gimmick that was based on the image of The Brawny Man. Vignettes for the character showed him doing "manly" things like chopping wood, shaving with a plain razor, and squeezing his own orange juice. After he made his full-time debut in October 1998, he faced X-Pac in the opening round of the tournament for the vacant WWF Championship at the Survivor Series, ending in a double countout and thus eliminating both men from the tournament. Regal then began a feud with The Godfather, but was taken off television soon after before subsequently checking into rehab in January 1999 and was released from the WWF in April.

Return World Championship Wrestling (1999—2000)

After checking out of rehab, Matthews was invited back into the wrestling world, making a somewhat brief return to WCW as Lord Steven Regal. His official pay-per-view return took place during Bash at the Beach in 1999 where he was one of many participants in the first ever Hardcore Invitational. On Nitro the following night, Regal, accompanied by both Fit Finlay and Dave Taylor, fought Billy Kidman. The fans reacted as if Regal had never left and straight after the bell began chanting "USA! USA!". Despite outside help from Finlay and Taylor, Regal was unable to pick up the win. Two weeks later he faced Mikey Whipwreck. Jimmy Hart's First Family came out to challenge The Blue Bloods at Road Wild for the Hardcore Trophy, causing Regal to lose the match. Nothing came of this challenge as neither the First Family or the Blue Bloods were featured on the Road Wild card. Similar to his previous run, much of Regal's performances took place in tag team bouts. He continued his role as a rule breaking villain and had small feuds with teams such as the Filthy Animals. In late February 2000, Regal faced off in a Career vs. Career match against "Hacksaw" Jim Duggan on Saturday Night for the Television Title. With WCW continuing to lose the ratings war with WWF, Regal lost the match and was again released.

Return to World Wrestling Entertainment (2000—present)

Commissioner (2000—2001)

Regal was once again hired by the WWF and sent to the developmental territory Memphis Championship Wrestling for a short time. After a match with Chris Benoit at the Third Annual Brian Pillman Memorial Show, he was brought up to the main roster and re-debuted on the September 18 episode of Raw is War. His new character was Steven William Regal (soon shortened to William Regal), a stereotypical English snob, hearkening back to his WCW character. As a villain, Regal had much more success, winning the European Championship. He later became the on-screen commissioner and self-proclaimed "Goodwill Ambassador" of the WWF and was given a comedy sidekick in Tajiri. During the WCW/ECW Alliance storyline, Regal became a villain by costing Kurt Angle the WWF Championship and joining the WCW Alliance. He was fired as commissioner by Linda McMahon, but Shane McMahon, who was the owner of WCW, hired him as the Alliance Commissioner. After the Alliance was defeated at Survivor Series in November 2001, Regal was forced to become the first member of Vince McMahon's "Kiss My Ass" club by kissing the left cheek of McMahon's ass so he could keep his job.

Intercontinental Champion and World Tag Team Champion (2002—2005)

In 2002, after an absence due to surgery on his nose, Regal returned and feuded with Edge. He won the Intercontinental Championship from Edge at the Royal Rumble in January, where he began using a set of brass knuckles in order to win matches. Regal defended the title against Edge again at No Way Out in a brass knuckles on a pole match before losing the title to Rob Van Dam at WrestleMania X8. Soon after, he beat fellow WCW alum Diamond Dallas Page for the European Championship on an April 2002 edition of SmackDown! In mid-2002, the World Wrestling Federation was renamed World Wrestling Entertainment, and the roster was divided into two separate "brands". During this time he was drafted to the Raw brand by owner Ric Flair. He was defeated by Spike Dudley in a match for the European Title, but won it back two weeks later to become a four time champion. He later lost the title to Jeff Hardy and later held the Hardcore Championship five times. He formed an alliance with Molly Holly before joining The Un-Americans, an anti-American villainous alliance consisting of Canadian wrestlers Lance Storm, Christian and Test. On the September 30, 2002 episode of Raw, every member of The Un-Americans lost their matches, causing the group to separate later in the night and break away into separate groups. Regal began teaming with Lance Storm, Christian formed a tag-team with Chris Jericho, and Test branched off into single competition. Storm and Regal won the World Tag Team Championship from Booker T and Goldust thanks to Regal's brass knuckles. They lost the titles to The Dudleys (Bubba Ray and D-Von) at the Royal Rumble, but regained the titles twenty four hours later, thanks to an impromptu match set up by Chief Morley after Regal and Storm had put Bubba through a table. Regal would later have to give up his title due to a heart condition (initially thought to be a stomach virus contracted on a recent WWE tour of India).

Eugene, the "mentally challenged" nephew of Raw General Manager Eric Bischoff, was placed in the care of Regal during his return to WWE. Initially dismayed at having to babysit Eugene, Regal eventually grew very fond of him and they became friends, becoming a fan favorite in the process. Regal was ordered by Bischoff to make Eugene lose so that he would leave WWE, but his friendship with Eugene caused him to try only half-heartedly to cost Eugene his match with Robert Conway. Despite this, Bischoff put Regal back on the active roster. Regal would later team with Eugene and win the World Tag Team Championship from La Résistance on the November 15, 2004 edition of Raw. Eugene legitimately injured himself at New Year's Revolution after botching a dropkick. This ultimately cost them the World Tag Team Championship, as Regal unsuccessfully attempted to defend the titles with announcer Jonathan Coachman as Eugene's stand in. The pair wrestled and lost a match against La Résistance at a house show, crowning them with their third reign. On February 4, 2005, Regal and old ally Tajiri defeated La Résistance to win the World Tag Team Championship on an episode of Raw, broadcast live from Tajiri's home country Japan. La Résistance entered in a feud with the champions, and repeatedly missed out on the titles during matches, mainly on Sunday Night Heat. During their last shot for the titles, La Résistance thought they had won back the titles, only to have the decision reversed by referee Mike Chioda due to the legal man not being pinned. After winning this match, an open challenge to any tag team was issued by Regal to try and win their belts. On the following episode of Raw, Regal and Tajiri successfully defended the belts against the debuting Romeo and Antonio, known collectively as "The Heart Throbs." At Backlash in May, Regal and Tajiri participated in a Tag Team Turmoil match in which four teams competed for the World tag team titles. Regal and Tajiri were eliminated by La Résistance who, in turn, were eliminated by Hurricane and Rosey, who became the new champions. Shortly before the 2005 ECW One Night Stand, Regal announced that he was joining Eric Bischoff's anti-ECW faction to invade the pay-per-view, and told Tajiri he had to make a choice, either to join with Regal or join with ECW. Tajiri responded by chanting, "EC-Dub! EC-Dub!" (the traditional ECW chant). Regal did indeed invade the ECW pay-per-view, along with many other WWE performers. This would turn him heel again as a result.

SmackDown! and various feuds (2005—2006)

On June 30, 2005, Regal was sent to SmackDown! as part of an eleven person trade during the draft. His first match on SmackDown! was on July 7 against Matt Morgan, in what was to be Morgan's final WWE match. It was interrupted before Regal was even able to enter the ring by The Mexicools. His first full match as part of the roster was a loss to Chris Benoit in a chain wrestling match on the July 16 episode of WWE Velocity. Having applied the Regal Stretch which Benoit managed to escape from, Regal eventually submitted to the Crippler Crossface.

On August 4, 2005, Regal was scheduled to go one on one with Scotty 2 Hotty, but the Mexicools came in and attacked both men. Two weeks later, they teamed up on SmackDown! against Psicosis and Super Crazy with Juventud in their corner. Halfway through the match, Regal betrayed Scotty by refusing to tag him and walked out of the ring with a smirk on his face, allowing the Mexicools to pick up the win. Two days later, Regal cut a promo telling the crowd that he had returned to his former self, referring to himself as a "scoundrel" and a "rogue". The promo ended when Scotty ran to the ring and attacked Regal. The following week, a match between the two was cut short when another Englishman, the debuting Paul Burchill, interfered to aid his countryman. Regal went on to take Burchill under his wing and tag with him on the hunt for the WWE Tag Team Championship, but the teams biggest exposure was a loss in a handicap match against Bobby Lashley at Armageddon.

On the February 3 edition of SmackDown!, Regal and Burchill told the "network representative" Palmer Canon that they no longer wanted to be a tag team so they could go their separate ways. During this discussion, Burchill informed Canon that his family heritage traced back to the pirate Blackbeard, and that he wanted to turn this into a pirate gimmick. Burchill, with this heroic persona, started a rivalry with former team mate Regal, who would try to convince Burchill to return to his ruthless ways. Regal faced Burchill, his first match as a pirate, and was defeated following Birchill's Walking the Plank move. Burchill once again defeated Regal in a match with the stipulation that Regal would have to dress like a "buxom wench" if he lost the match. Lady Regal, as SmackDown! announcers jokingly referred to him, had no choice but to dress up like this until Burchill lost a match. This stipulation ended after Burchill abandoned Regal during a match that saw Regal and Burchill defeated by the Gymini tag team.

King Booker's Court and reunion with Dave Taylor (2006—2007)

Regal continued to wrestle in a lower mid-card status, the highlight of which saw Regal turn face for one night only as he faced the then-reigning United States Champion, JBL in a losing effort while in England. Soon after Booker T became King Booker after becoming King of the Ring and Regal joined King Booker's Court, playing the role of a town crier. As a member of the Court, Regal helped Booker in his feud against Bobby Lashley, occasionally teaming up with fellow Court member Finlay in tag team matches. However, during this time, Regal also feuded with Finlay for the WWE United States Championship. Regal was knighted by King Booker and changed his ring name to Sir William Regal. At No Mercy, Regal lost to a returning Chris Benoit in a match, turning his back on the King's Court afterwards by knocking down King Booker with a left hand to the face after Booker slapped him and called him useless. During the broadcast, Regal was involved in a backstage segment with Vito in which he accidentally exposed his penis for a brief second. WWE.com issued an apology for the incident the next day.

Twelve days after No Mercy, Regal stated that while he had once been one of the world's greatest wrestlers, he had since become a doormat for other SmackDown superstars. He referred to being dressed as a buxom wench for a pirate, the aforementioned locker room incident with Vito, and being knighted by a false king as examples. After announcing he was finished being a whipping boy, he introduced his old tag team partner Dave Taylor, and the two went on to easily defeat the team of Scotty 2 Hotty and Funaki. Though the pair reformed their previous tag team, they did not reuse the Blue Bloods gimmick, instead portraying themselves as sadistic fighters. However, the team was quickly put into jeopardy in their second match together when Taylor suffered a torn meniscus in his left knee leaving him injured. Taylor took a more relaxed role for a couple of weeks as a corner man for Regal and only wrestled in a few short house show matches. Taylor quickly healed from his injury and the pair feuded with WWE Tag Team Champions Paul London and Brian Kendrick. After defeating London and Kendrick on several occasions, at Armageddon, they took part in a 4-way ladder match alongside Johnny Nitro and Joey Mercury and The Hardys. London and Kendrick coming out on top after Joey Mercury suffered a serious facial injury. On the May 25 edition of SmackDown!, Regal and Taylor competed in a number 1 contenders match for the WWE Tag Team Championship against London and Kendrick, which they lost after Deuce 'n Domino interfered, making both teams the number one contenders. This interference led to a triple threat match the next week on SmackDown!, in which Deuce 'n Domino retained the title.

General Manager and King of the Ring (2007—2009)

On June 17, Regal was drafted back to the Raw brand during the Supplemental Draft, ending his tag team with Dave Taylor. On July 2, Regal served as Interim General Manager of Raw, filling in for Jonathan Coachman. While General Manager, Regal introduced the Beat the Clock Sprint to Raw, which was used to determine who would challenge John Cena for the WWE Championship at the 2007 Great American Bash.

On the August 6 edition of Raw, Regal became the new General Manager after winning an over the top rope battle royal featuring other participants from the Raw roster. He began incorporating game shows into Raw while general manager. On the September 3 episode of Raw', Regal was attacked by WWE Champion John Cena in retaliation for rewarding Randy Orton with a WWE title shot after Orton had kicked John Cena's father in the head the previous week. Regal was missing from Raw programming for one month due to this attack, making his return by siding with Vince McMahon. On New Year's Eve, Triple H was scheduled to face Ric Flair, in which Flair's win or retire ultimatum was still active. Regal announced that if Triple H lost the match in any way, he would not participate in the Royal Rumble match at the 2008 Royal Rumble. This was to give Triple H a reason to want to win the match rather than avoid ending the career of his best friend and idol. Regal was scheduled to compete against Hornswoggle that night with Mr. McMahon at ringside. McMahon tossed Regal some brass knuckles during the match and encouraged him to use them on Hornswoggle, but he let Hornswoggle go and left the ring. During the Flair versus Triple H match, Triple H performed the Pedigree on Flair and appeared to be going for the pin when Regal suddenly punched Flair in the face with the brass knuckles. This gave Flair the win by disqualification, ensuring that he could continue to wrestle and that Triple H would not be part of the Royal Rumble. As a result of Regal's actions towards Triple H, the following week on Raw Roulette, Regal lost a First Blood match to Triple H after several right hands to Regal's forehead. A few weeks later, he made the Raw Elimination Chamber match for No Way Out. He later turned face for one night only while on a European tour, by facing Randy Orton in a match to try and teach him some respect.

The following week, Regal won the 2008 King of the Ring Tournament, on a special three hour edition of Raw, where he defeated Hornswoggle, Finlay and CM Punk all by submission. Regal's coronation ceremony the next week was interrupted by the returning Mr. Kennedy. A few weeks later Regal lost a Loser Gets Fired match to Mr. Kennedy, after which, Regal was kayfabe forced to leave WWE. In reality, Regal was suspended on May 20, 2008, for sixty days for his second violation of the company’s Substance Abuse and Drug Testing Policy. On July 28, 2008, Regal returned from his suspension as a "free agent" during an episode of Raw, where he was defeated by then World Heavyweight Champion CM Punk.

Regal began a mini-feud with Jamie Noble after he took an interest in Noble's romantic interest Layla, prompting him to attack Regal. Both men picked up victories in consecutive weeks, before Regal won their third match, departing with Layla at his side. Regal's feud with Noble escalated the subsequent week when Layla declared that Noble was a loser and that she found a man worthy of her in Regal. However, the feud was short lived.

On the November 3, 2008 episode of Raw, Regal won an over-the-top battle royal to face Santino Marella for the Intercontinental Title, and the next week in Manchester, England, Regal defeated Marella in a 40 second squash match to win his second Intercontinental Title. Later, he entered into a feud for the title with number one contender CM Punk. On the January 5 edition of Raw, Regal lost to Punk via disqualification after he grabbed the referee's shirt. Due to this, Stephanie McMahon awarded Punk a rematch the following week, with the stipulation that if Regal was disqualified, Regal would lose the Intercontinental title, but this time Punk was disqualified. McMahon awarded Punk another rematch, this time a No Disqualification match on January 19 episode of Raw, Punk won the match and the title. Regal got a rematch but lost the match when Punk hit the Go To Sleep.

Following the Draft, Regal was left alone on the Raw brand as his on-screen manager Layla was drafted to the SmackDown brand. At Extreme Rules, Regal unsuccessfully challenged Kofi Kingston for the WWE United States Championship along with Montel Vontavious Porter and Matt Hardy, Kofi Kingston retained the United States Championship by pinning Regal.

ECW and The Ruthless Roundtable (2009—2010)

William Regal was traded to the ECW brand on June 29, 2009. In his first match on ECW on SyFy on June 30, 2009, he teamed with Vladimir Kozlov to defeat Tommy Dreamer and Christian.

On the August 11 edition of ECW on SyFy, Regal defeated Tommy Dreamer to become number one contender for the ECW Championship. A week later, Regal teamed with Vladimir Kozlov to face Christian and Ezekiel Jackson, with the end of the match involving Jackson turning on Christian, allowing Regal to pin Christian for the victory. The end result of a new stable, referred to as "The Ruthless Roundtable". At SummerSlam 2009, Regal challenged Christian for the ECW Championship, but was unsuccessful after losing to Christian in just 8 seconds. Regal then challenged Christian to a rematch for the title at WWE Breaking Point, but was once again unsuccessful. Regal received another shot for the ECW Championship on the November 10 edition of ECW on SyFy in Sheffield, England, but was once again unsuccessful. Regal and Jackson eventually turned on Kozlov for being the 'weak link'. After that he formed an alliance with Ezekiel Jackson. On the final episode of ECW on SyFy, Regal helped Ezekiel Jackson defeat Christian to become the new and final ECW Champion.

NXT and Return to Raw (2010—present)

In February 2010, Montel Vontavious Porter was announced as the WWE Pro to mentor NXT Rookie, Skip Sheffield on WWE NXT, but MVP was replaced by Regal before the show debuted. Regal made his debut on the March 2 edition NXT, teaming with his rookie Skip Sheffield in a losing effort against Matt Hardy and Justin Gabriel. On the March 30 edition of NXT, Regal teamed with Christian, Carlito and The Miz to take on R-Truth, Matt Hardy, CM Punk and Wade Barrett in a 8-man tag match, in which his team was defeated. On the April 13 edition of NXT, Regal won his first match on the show, defeating Daniel Bryan. On the May 10 edition of NXT, Regal's rookie Sheffield was eliminated from the competition.

On February 23, 2010, Regal's profile was moved from ECW to Raw, signalling his return to the brand. On February 25, Regal competed in a tag match on WWE Superstars teaming with Jack Swagger to defeat Chris Masters and Santino Marella confirming his move to Raw.

On the March 5 episode of WWE Superstars, Regal went up against Evan Bourne in a losing effort. On the March 8 episode of Raw, Regal once again faced Evan Bourne, this time in a Money in the Bank Qualifying match in a losing effort. Regal competed in the 26-Man Battle Royal that was held before WrestleMania XXVI, which was won by Yoshi Tatsu.

On the May 3 episode of Raw, Regal reunited with Vladimir Kozlov in a losing effort against The Hart Dynasty. On the May 31 Raw, Regal was attacked by Kozlov during a mixed tag match, ending their reformation. On the June 14 Raw, Regal temporarily turned face while helping other superstars chase off the NXT season one rookies, know as The Nexus, who had tried to attack John Cena. Later on the same show, Regal had a match against Santino Marella but failed to win due to Vladimir Kozlov being the Special Guest Referee and giving Marella a fast count.

In late July, Regal started to team with Zack Ryder, but lost in every match they teamed up in. After a losing streak that lasted five months, Regal gained his first victory since April by defeating Goldust on the August 26 edition of WWE Superstars. On the September 13 Raw, Regal was defeated by Goldust in a Trading Places Match (Regal had to wear Goldust's attire and Goldust had to wear Regal's), which was decided by the Raw Roulette Wheel.

He has been married to his wife Christina since 1986. They have three sons: Daniel (born 1988), Dane (born 1991) and Bailey (born 1996). His actual accent (West Midlands) is very different from the one he uses on television as he is from Codsall Wood, Staffordshire. He has a tattoo on his left leg which says "Made In England" and a rose with his wife's name on his left arm. Matthews participated in an episode of The Weakest Link, winning two of the first three rounds and eventually finishing third. In the final three he was up against husband and wife Triple H and Stephanie McMahon. His pets include two snakes, eight lizards, a tortoise, three cats, and two dogs. He claims the reason he owns so many pets is because "Humans disgust me. Vile creatures".

In 2003 Darren was misdiagnosed with what was in actual fact a heart defect which meant the right side of his heart was beating out of sequence with the left. This allowed large volumes of fluid to build in his body. After undergoing specialist treatment which involved stopping his heart and months of anti-blood clot treatments, he returned to wrestling in April 2004. During his illness and recovery he put on, and then lost, 40 pounds in weight.

While in WCW, he was arrested during a flight from Japan back to the US when he got drunk on the flight and urinated on a stewardess. By Matthews' account in his book, he claims that he was so drunk that he could not remember the incident and woke up in a cell in Anchorage, Alaska. On August 30, 2007, Sports Illustrated named Matthews, along with nine other superstars, found to be given illegal steroids not in compliance with the WWE Talent Wellness program. Matthews received stanozolol, somatropin, genotropin, and anastrozole between November 2004 and November 2006.