Throughout the late '80s up until the mid-90s, two names encapsulated sports entertainment and where it was heading. When The Hart Foundation and The Rockers both debuted, it was clear Bret Hart and Shawn Michaels were far better than just a couple of guys in a couple of tag teams. Once the lumbering giants got out of the way, The Hitman struck gold first.
Bret Hart winning the world title opened up the door to “smaller guys” and workhorses winning the WWE title. Shawn Michaels would follow suit and two men whether they were feuding or not both opened doors for the rest of the WWE locker room.
Bret Hart held the WWE Championship five times and another two in WCW, while Shawn would win four world titles in WWE. Since these two legends' careers are often discussed in parallels, here are all their reigns, ranked from worst to best.
11 Bret Hart - Defeated Goldberg / Lost To Goldberg’s Kick, Vacated
Following a controversial win over Goldberg at Starrcade 1999, Bret Hart vacated the WCW title out of respect for Goldberg, offering for the two to face off in a rematch on Nitro for the vacant title. The Hitman would turn heel during this match, aligning with The Outsiders to form the nWo 2000.
Whatever buzz this version might have garnered was cut short thanks to Goldberg and Hart’s match the night before at Starrcade. Goldberg kicked The Hitman right in the head giving him a concussion, from which Bret never fully recovered, ultimately ending his career.
10 Bret Hart - Won Mayhem Tournament / Vacated The Title
WCW had way too many irons in the fire to strike the Bret Hart one while he was hot. He was the biggest name and hottest property in the industry after Montreal. But it still took WCW years to put the title on him.
At the inaugural Mayhem event, Bret Hart won his first WCW title in front of his fellow countrymen. Just one month later, in typical WCW fashion (and Vince Russo booking), the wheels fell off. Thanks to the melee between Goldberg and Bret Hart at Starrcade, the next night on Nitro, the title was vacated.
9 Bret Hart - Defeated Vader, Austin, Taker / Lost To Sid
After Stone Cold cheated to win the 1997 Royal Rumble and after HBK lost his smile, the WWE title was vacant, as was the WrestleMania title shot. The title was decided in a Fatal Four Way at the aptly titled, IYH: Final Four.
Bret Hart was able overcome the odds and capture his fourth WWE title. One night later on Raw, thanks to interference from The Texas Rattlesnake, Bret Hart was defeated by Sycho Sid, marking his shortest world title reign.
8 Shawn Michaels - Defeated Sid / Lost To His Smile
After losing to Sid in Madison Square Garden and having his mentor taken out, Shawn Michaels vowed to return to his hometown of San Antonio to defeat Sid for the title at the Royal Rumble; which is exactly what he did. Michaels was able to overcome Sid and avenge the assault on José Lothario. Less than a month later, Shawn had gotten some bad news about his knee and was told he’d supposedly have to retire. He would forfeit the title on Raw and deliver the now infamous “lost my smile” speech.
7 Bret Hart - Defeated Diesel / Lost To Shawn Michaels
Less than a week after beating Bret Hart for the WWE Championship at the 1994 Survivor Series, Bob Backlund lost the title in eight seconds to Diesel. For the next year, Big Daddy Cool defended the WWE title, until he ran afoul of Bret Hart at the 1995 Survivor Series. The Hitman was able to topple the big man in what many argue was Kevin Nash's best match of his career. However, this reign was just meant to set up the big Hart/Michaels showdown. In just a few short months, Bret Hart and Shawn Michaels’ date with destiny at WrestleMania XII was on the horizon.
6 Shawn Michaels - Defeated Triple H, RVD, Y2J, Kane, Booker T / Lost To Triple H
After four years, Shawn Michaels entire life was different, but he would return at SummerSlam 2002. Several months later when it was announced that Triple H would defend the world title in the first ever Elimination Chamber, HBK was part of the festivities as well. He vowed to make sure Triple H wouldn’t retain the title and wound up winning the title himself. One month later at Armageddon, Shawn Michaels entered the Three Stages Of Hell with Triple H. After nearly forty five minutes of hell, HBK was unable to retain the title and Triple H was once again the man. This would be the last world title reign of HBK's career.
5 Shawn Michaels - Defeated Bret Hart / Lost To Stone Cold Steve Austin
Montreal - everyone remembers the bad ending, but before that happened, Bret Hart and Shawn Michaels were having a brawl for the ages. This controversial title win set Michaels up as the no.1 heel on the WWE roster. As for the reign that ensued, The Heartbreak Kid would defend the title against Ken Shamrock before suffering huge back injury in his Casket Match with The Undertaker.
Michaels' career was then on hiatus after losing the WWE title to Stone Cold Steve Austin at WrestleMania XIV, marking the beginning of The Attitude Era.
4 Bret Hart - Defeated The Undertaker / Lost To Shawn Michaels
No matter how it ended, 1997 was arguably the best year of The Hitman's career. The Hart Foundation was rebuilt and Bret Hart was a newly minted heel and the very best in the company. He rode that wave to SummerSlam and defeated The Undertaker to win his record-tying fifth world title. Several months later, Bret, Shawn, and the entire industry would never be the same as WWE would wind up with the most controversial moment in their history.
3 Bret Hart - Defeated Ric Flair / Lost To Yokozuna
While he was already a two time IC champion, Bret Hart truly became a made guy when he defeated Ric Flair for the WWE world title at a house show in Canada. For the first time in about ever, the company decided to go with a so-called smaller guy as the champion. But Bret was deserving, as he had spend nearly a decade in the company. During Bret’s first run, he had a feud with Razor Ramon, culminating with their match at the 1993 Royal Rumble. Bret would get to defend the title at WrestleMania IX, albeit in a losing effort to Yokozuna.
2 Shawn Michaels - Defeated Bret Hart / Lost To Sid
Considering he was the first to break through the smaller guy ceiling, Shawn Michaels beating Bret at WrestleMania XII was treated as a huge moment. For the next several months, Shawn Michaels then went on a tear, having marquee matches with anyone and everyone, including Diesel and Mankind in an instant classic at Mind Games.
HBK’s first title loss was against his former heater, Sycho Sid at the 1996 Survivor Series, who was actually getting cheered in MSG against the babyface Shawn.
1 Bret Hart - Defeated Yokozuna / Lost To Bob Backlund
After losing to Yokozuna at WrestleMania IX, Bret Hart spent a year scratching and clawing his way back to the mountaintop to topple the Mighty Sumo at WrestleMania X. Bret would spend the next several months waging familial war with Owen and having Raw’s first great classic against the 1-2-3 Kid. Bob Backlund returned during this time and after a loss to The Hitman, he snapped and went insane. Eventually Mr. Backlund was able to defeat Bret for the title after an award winning performance from Owen, feigning concern for his brother, locked in the Chicken Wing.