Paul made his first appearance in February 1991 when Brother Love, who originally managed The Undertaker, passed him on to be managed by Paul Bearer. Paul Bearer took on a spookier, ghastlier character as time went on and referred to The Undertaker as "My Undertaker". Pringle played the character for over thirteen years. As Undertaker's manager, as a heel and later a face for over five years, he was a mentor to The Undertaker, playing a major role in his entrances by guiding him to the ring, undoing his tie, and collecting his trench coat and hat. Bearer also hosted the WWF talk show segment entitled The Funeral Parlor, which included memorable segments such as the Ultimate Warrior being locked inside a casket, among others. Eventually Bearer turned heel again by betraying his long-time friend at SummerSlam 1996 to align himself with The Undertaker's arch-enemy, Mankind. While managing Mankind, his new protege always referred to him as "Uncle Paul". During this time, Bearer would also enlist the services of The Executioner and Vader to do battle against The Undertaker.
In April 1997 at In Your House Revenge of the Taker, The Undertaker set Bearer's face ablaze using a fireball. As a result, Bearer's head was bandaged for a time before changing his looks, shedding the makeup of ghostly pallor and jet-black hair to his natural brown hair and less make-up. No longer using his ghostly appearance and mannerisms, he became loudmouthed and shrill. Around mid 1997, Paul Bearer blackmailed The Undertaker (WWF Champion at the time) into being his protege again by threatening to reveal a deep, dark secret involving him, often making references to "the fires of Hell". Feeling he had no choice, The Undertaker accepted. While managing The Undertaker this time around, Bearer was very unpleasant toward him, harassing and nagging at him constantly. Eventually, Undertaker lost his patience and refused to allow Bearer to continue being his manager, leading Bearer to reveal the secret.
The secret suggested that Bearer had a traumatic past with The Undertaker which long preceded Brother Love's joining the two in January 1991. The secret, which involved the Undertaker's family, was: The Undertaker's mother had an affair with Paul Bearer and as a result, gave birth to a younger half-brother of The Undertaker, named Kane. Throughout The Undertaker's childhood and teen years, he lived in a funeral home with his parents and half-brother. According to Paul Bearer, The Undertaker killed his parents and caused his half-brother's face to be bruised and scarred by setting the funeral home ablaze. At the time throughout mid to late 1997, The Undertaker denied all this, claiming it was his younger half-brother's fault. Bearer accused The Undertaker of being a "murderer" and "liar". Because of the fire incident, The Undertaker thought his younger half-brother and Bearer's illegitimate son had been dead for years, that is, until Bearer introduced Kane in October 1997 at In Your House Badd Blood; during which, Kane would cost The Undertaker a Hell in a Cell match against Shawn Michaels. This led to an intense, bitter rivalry between The Undertaker and Kane with Bearer very much involved.
Bearer and The Undertaker became a team once again as heels toward the end of 1998 when Bearer betrayed his own son, Kane, in favor of managing The Undertaker once again. Once becoming a heel with Bearer, The Undertaker shamelessly admitted to setting the funeral home ablaze for which he had initially claimed was an accident or blamed Kane. Shortly thereafter, Bearer and The Undertaker formed the Ministry of Darkness. Bearer had somewhat reverted back to his original appearance once in the Ministry of Darkness, having jet-black hair and mustache. Both he and The Undertaker departed from the WWF unceremoniously in September 1999 as a result of The Undertaker suffering an injury.
In early 2000, Bearer, who turned face once more briefly, returned to WWF TV as Kane's manager, but he retired from on-screen performing shortly after WrestleMania 2000. Later that year, he went backstage to serve as a WWF road agent, stage manager, and talent scout. His contract with WWE ended in October 2002.
Paul reappeared in March 2004 at WrestleMania XX, alongside Undertaker in a match against Kane. Paul Bearer also appeared on TV as The Undertaker's manager.
In spring of 2004, Paul Bearer was kidnapped by The Dudley Boyz under the direction of Paul Heyman. This was set up in order to temporarily write Bearer out of WWE story lines because he had to undergo emergency gallbladder surgery after suddenly developing gallstones, a common side effect of gastric bypass surgery.
For the June 27, 2004 pay-per-view The Great American Bash, a match pitting Undertaker against both of the Dudley Boyz was booked. Paul Bearer would be encased in a glass crypt backstage, covered up to his chest in cement. In the storyline, Heyman demanded that Undertaker throw the match or else see Bearer suffocated in cement. By the time of the pay-per-view, Bearer had recovered from his latest operation and would appear on-screen.
Undertaker won the match but proceeded afterwards to pull the lever that sent cement into the crypt, completely burying Paul Bearer, suffocating him. (Bearer was not really at the event. The WWE had recorded footage of Paul Bearer in the crypt before the event. During the event, there was a stunt double in the crypt the whole time. That's why the TV audience could only see Paul Bearer and the crypt he was in – since he wasn't there, they couldn't actually show anyone on screen with Bearer). This shot ended the PPV and caused numerous complaints toward WWE, as in essence they had shown a simulated murder. The live audience, however, saw an extended ending in which Bearer surfaced for air and was carried from the arena on a stretcher. On the following week's SmackDown!, Bearer was acknowledged to be alive, although gravely injured, for storyline purposes. The rehearsal taping earlier in the day of the Bash – with Undertaker ad-libbing and only half of the stunt complete, in an empty arena – was leaked onto the internet dirt sheets and actually broadcast live by accident in many of the TV markets. As he had two years remaining on his contract, however, Bearer was used as a booker for the company up until WWE decided to terminate his contract on April 11, 2005.
On the September 24 episode of SmackDown, Bearer returned after being brought out in a casket. Bearer would help The Undertaker, who was feuding with Kane over the World Heavyweight Championship, by restoring Undertaker's powers with the urn. Bearer would officially become Undertaker's manager again by accompanying him to the ring for his match against Kane for the title at the Hell in a Cell pay-per-view. During the match however, Bearer once again turned on Undertaker, after shining a light in his eyes when he was about to tombstone Kane. Bearer would then let Kane use the urn as a weapon to help him win the match, thus, turning Bearer heel. On the October 15 episode of SmackDown, Bearer challenged Undertaker to face Kane in a Buried Alive Match for the World Heavyweight Championship at Bragging Rights, to which Undertaker accepted by attacking Kane. At Bragging Rights, Kane once again defeated Undertaker after interference by Bearer, who was almost thrown in the grave by Undertaker, and Nexus, who helped Bearer and Kane bury Undertaker.
Kane would then enter a feud with Edge, after he was named the new challenger to Kane's World Heavyweight Championship at Survivor Series. On the November 12 episode of SmackDown, Bearer cost Edge his match against Nexus member David Otunga. After the match, Edge would kidnap Bearer by strapping him in a wheelchair. Later that night, Edge would use Bearer to cost Kane his match against The Big Show. The following week, Edge would torment Bearer throughout the night by throwing a dodgeball at him and force feeding and throwing food all over him. Edge would then use Bearer to call for Kane in the parking lot, but Kane wasn't able to get Bearer in time as Edge attacked him and drove off with Bearer. On the November 26 episode of SmackDown, Kane demanded that Edge to let Bearer go, but Edge refused. Kane would then try and track down Bearer, but was unable to find him. Kane would then offer a second title shot to Edge, which he accepted, but continued to keep Bearer with him. At the end of the night, Edge lured Kane to the parking lot, where Edge would drive over a dummy version of Paul Bearer, with the actual Paul Bearer in the backseat of the car. On the December 3 episode of SmackDown, Edge continued his mind games with Kane by pushing a dummy version of Paul Bearer down some stairs. Then, after Edge defeated Kane in a non-title match, he brought out a Paul Bearer lookalike. Kane then went to search for Bearer again, but Edge drove away in a truck with Bearer tied up on the back. The following week, Kane begged Edge to return Bearer, but Edge once again refused. Kane then refused to participate in the main event that night and once again searched for Bearer. After what he thought was a dummy version of Paul Bearer on top of two ladders, Kane pushed them over. Afterward, Kane saw that he pushed the actual Paul Bearer off the ladders onto the concrete floor, thus, injuring him. This would be Bearer's last appearance to date on SmackDown as he was written out of the storyline.
In April 2012, Bearer returned for a brief stint as a part of Kane's ongoing feud with Randy Orton. He was kidnapped by Orton and then stuck in a storage freezer while strapped to a wheelchair. Kane later came for Bearer, only to roll him back into the freezer and saying, "I'm saving you...from me."
Sadly, on March 5, 2013, Paul Bearer died from a blood clot.
The March 11th episode of Raw was held as a tribute to Bearer, The Undertaker paid tribute but was interrupted by CM Punk, his WrestleMania 29 opponent. Punk then mocked Bearer over the few weeks against both Kane and The Undertaker, including stealing his urn and attacking Kane with it. Punk even went as far as to do 'tricks' with it, including dropping it and mocking Undertaker with it using Bearer's voice. On the April 1st episode of Raw, Punk dressed as a druid while Paul Heyman dressed up as Paul Bearer, Undertaker attacked the wrong druid while Punk attacked him and poured the ashes of the urn on The Undertaker. At WrestleMania, Undertaker defeated Punk and took back the urn dedicating his victory to Paul Bearer.
On the March 3, 2014 episode of Raw it was announced that Paul Bearer would be inducted into the WWE Hall Of Fame.