Dudley received a tryout with Extreme Championship Wrestling in September 1995, appearing as Mongo, the bodyguard of Bill Alfonso. After impressing ECW owner Paul Heyman by taking a chokeslam from wrestler 911, Mongo was hired. He was recast as Buh Buh Ray Dudley, the stuttering, dancing, overweight, hillbilly member of the sprawling Dudley family. The unusual spelling of "Bubba" was a result of his stutter. In saying his name, Buh-Buh would stutter, causing him to say "My name is Buh-buh-buh-buh" until Big Dick Dudley struck him in the chest, at which point he would snap out "My name is Bubba Ray Dudley!".
On April 13, 1996, D-Von Dudley debuted in ECW and began feuding with the other members of the Dudley Family (his kayfabe half-brothers), claiming that their comedic antics were not the way true Dudleys should act. D-Von eliminated Dances With Dudley, Dudley Dudley, and Chubby Dudley before joining forces with Buh Buh Ray, Big Dick, Sign Guy Dudley, and Joel Gertner. Known collectively as The Dudley Boyz, Buh Buh Ray and D-Von dominated the ECW tag team division, winning the ECW World Tag Team Championship a record eight times and defeating the four major tag teams in ECW: The Public Enemy, The Eliminators, The Gangstas, and Sabu and Rob Van Dam. Buh Buh Ray, D-Von, and Gertner all achieved a degree of infamy for their vitriolic interviews, which antagonized audiences to a point of near riot.
In 1999, Buh Buh Ray and D-Von left ECW and joined the World Wrestling Federation, where the "Buh Buh" stutter-spelling of "Bubba Ray Dudley" was rescinded. Throughout 2000 and 2001, the Dudley Boyz engaged in a three-way feud for the WWF Tag Team Championship with The Hardy Boyz and Edge and Christian. The feud incorporated two critically acclaimed Tables, Ladders, and Chairs matches, the first at SummerSlam in 2000 and the second at WrestleMania X-Seven. While they were initially heels, one of the things Bubba Ray was known for was driving women through tables including WWE Divas Terri, Mae Young, Lita, Trish Stratus, Tori, Torrie Wilson, Stacy Keibler and Jazz. The Dudley Boyz were soon cheered by the crowd and were turned face in early 2000. On the December 28, 2000 episode of SmackDown!, Bubba received a title shot against WWF Champion Kurt Angle, which he lost. In early 2001, The Dudleys were joined in the WWF by Spike Dudley.
In mid-2001, the Dudley Boyz turned heel once again by joining The Alliance, a large stable of former ECW and World Championship Wrestling (WCW) wrestlers led by Shane McMahon and Stephanie McMahon-Helmsley who attempted to take over the WWF (Spike, along with other ECW alumni, did not join The Alliance). The ECW-WCW invasion ended at Survivor Series, when five WWF wrestlers defeated five Alliance wrestlers in a match to determine the ownership of the WWF. The Alliance disbanded and its members left the WWF, but the Dudley Boyz retained their jobs due to their possession of the WWF Tag Team Championship, which they had unified with the WCW Tag Team Championship that night.
Following WrestleMania X8, in May 2002 the WWF was renamed "World Wrestling Entertainment" (WWE) and the roster was divided into two brands, Raw and SmackDown!. The Dudley Boyz were separated when Bubba Ray was drafted to Raw and D-Von to SmackDown!. On Raw, Bubba Ray found moderate success as he competed for the WWE Hardcore Championship, formed a tag team with Spike, and even competed in a World Heavyweight Championship match against Triple H. D'Von's new gimmick on SmackDown! failed to get over, however, and he was reunited with Bubba Ray and Spike on November 17, 2002 when he returned to the Raw brand.
The Dudley Boyz became a staple in the Raw tag team division over the next sixteen months, feuding with teams such as 3-Minute Warning, La Résistance, and various combinations of The Un-Americans. They held the WWF World Tag Team Championship several more times before being traded (along with Booker T) to SmackDown! on March 22, 2004 in exchange for Triple H. Shortly after arriving on SmackDown!, the Dudley Boyz turned heel once again, siding with Paul Heyman and feuding with Rob Van Dam and Rey Mysterio. On May 27, the Dudley Boyz kidnapped Paul Bearer, the manager of Heyman's enemy The Undertaker. On June 27 at The Great American Bash, The Undertaker defeated the Dudley Boyz in a handicap match. In July, the Dudley Boyz reunited with Spike. For the remainder of the year, they assisted Spike in his matches for the WWE Cruiserweight Championship. They also won the WWE Tag Team Championship one more time. In early 2005, the Dudley Boyz were removed from WWE television while the WWE creative team attempted to devise an angle for them.
The Dudley Boyz returned to WWE television in June 2005 in order to promote ECW One Night Stand, an ECW reunion show. In the weeks preceding One Night Stand they, along with several other ECW alumni, vied with General Manager Eric Bischoff and his "anti-hardcore crusaders". At One Night Stand on June 12, the Dudley Boyz defeated Tommy Dreamer and The Sandman in the main event of the night after driving Dreamer through a flaming table. On July 5, 2005, WWE announced that it had opted not to continue contract renewal negotiations with the Dudley Boyz.
Bubba Ray made a one night appearance with WWE at the 2015 Royal Rumble, entering as a surprise entrant at number 3. He eliminated The Miz and R-Truth before being eliminated by Bray Wyatt.
On the August 24, 2015 episode of Raw, he and D-Von Dudley made a surprise return to the WWE, reviving their Dudley Boyz tag team persona. They attacked the WWE Tag Team Champions, The New Day, and gave a 3D through a table to Xavier Woods. On the August 27 episode of SmackDown, they defeated The Ascension and after the match they put Viktor through a table. On the August 31 episode of Raw, they wrestled their first match on the show in 10 years against The New Day in a winning effort. Following the match, they would attempt to 3D Big E through a table, but Big E would be saved by Woods and Kofi Kingston. On the September 3 episode of SmackDown, The Dudley Boyz defeated The Prime Time Players. At both Night of Champions, and Live from Madison Square Garden, the Dudley Boyz challenged The New Day for the WWE Tag Team Championship, but would win both matches by disqualification, which allowed New Day to retain their titles. At Hell in a Cell, the Dudley Boyz would challenge for the titles again, where they would be defeated by New Day. At Survivor Series, the Dudley Boyz would team with Goldust, Neville and Titus O'Neil to defeat Stardust, The Ascension, The Miz and Bo Dallas in a 5-on-5 traditional Survivor Series elimination tag team match.
From the November 23 episode of Raw, the Dudley Boyz began a short rivalry with The Wyatt Family, and later aligned themselves with the returning Tommy Dreamer and Rhyno in the feud. At TLC: Tables, Ladders and Chairs, The Wyatt Family defeated The ECW Originals in an eight-man elimination tables match.
On the December 31 episode of SmackDown, the Dudley Boyz teamed with Kalisto in a winning effort against The New Day in six-man tag team match. They would face The New Day in a rematch on the January 4, 2016 episode of Raw in a losing effort. At Royal Rumble, the Dudley Boyz would compete in a Fatal 4-Way tag team match on the pre-show for a spot in the Royal Rumble match itself, with the match being won by Mark Henry and Jack Swagger.
On the February 8 episode of Raw, the Dudley Boyz attacked The Usos after a match involving them against The New Day and Mark Henry, thus turning heel in the process. Explaining that they did not come back to WWE to be a "nostalgia act" and reminding the fans that they are "the baddest tag team on the planet", the Dudley Boyz abandoned using tables. In the following weeks, the Dudley Boyz and The Usos began a feud, setting up a tag team match between the two teams at WrestleMania 32, where the Dudley Boyz lost to The Usos. The following night on Raw, the Dudley Boyz defeated The Usos in a tables match, breaking their vow to never again use tables and officially ending the feud. Afterwards, the duo were interrupted by the debuting Enzo Amore and Colin Cassady, who proceeded to insult them and ignite a new feud. In a tournament set up by Shane McMahon to determine the new number 1 contenders to the WWE Tag Team Championship, they would defeat The Lucha Dragons to advance to the semi-finals, where they clashed with Enzo Amore and Colin Cassady in a losing effort. On July 19 at the 2016 WWE draft, the Dudley Boyz were drafted to Raw. At SummerSlam, they would lose to Sami Zayn and Neville.
The Day after SummerSlam, the Dudley Boyz announced that they were departing from WWE on that night's Raw. During their farewell segment, they were confronted by The Shining Stars. After receiving insults from The Shining Stars, the Dudley Boyz attacked them, turning face once again in the process. As they set up Primo for a 3D through a table, Luke Gallows and Karl Anderson attacked both Bubba Ray and D-Von, sending D-Von through the table.
On January 22, 2018 on the occasion of Raw 25 Years, the Dudley Boyz returned for one night only, by interrupting a fight between Heath Slater and Rhyno and Titus Worldwide, giving a Whassup? and a Dudley Death Drop to Heath Slater through a table.
The Dudley Boyz were inducted into the WWE Hall of Fame class of 2018.
At Wrestlemania XL on April 7, 2024, Dudley made an appearance as the special guest referee for the Philadelphia street fight between The Final Testament's Karrion Kross, Akam and Rezar, and Bobby Lashley and the Street Profits. After numerous spots collaborating with the latter, Lashley and the Street Profits defeated The Final Testament. At NXT Halloween Havoc on October 27, Dudley appeared as a host of the countdown show alongside Dave LaGreca. Ridge Holland, who was due to have an Ambulance match at the event, interrupted Dudley and LaGreca twice. After the NXT Championship match main event, Holland came out and attacked NXT Champion Trick Williams. Dudley then ran into the ring to save Williams from Holland and Ethan Page, who was Williams' opponent for the main event. On the following episode on NXT, Dudley appeared in a segment with Williams, where Dudley initially declined the latter's offer to be his tag team partner against Ridge and Page at NXT 2300. Later on however, after being saved by Williams from an attack by Holland and Page, Dudley changed his mind and accepted Williams' offer. At NXT 2300 on November 6, Dudley and Williams lost to Holland and Page. After the match, Dudley and Williams put Page through a table that was brought to the ring by D-Von, reuniting the Dudley Boyz in the process.