For months, WWE Chairman Mr. McMahon was said to have fathered an illegimate child (which.... based on what we now know may not be far from the truth). On September 10, 2007, McMahon's little bastard was finally revealed to be... the former Little Bastard known as Hornswoggle.

On the April 7, 2014 edition of Raw, newly minted WWE Hall of Famer The Ultimate Warrior delivered an epic promo about how "every man's heart one day beats its final beat; his lungs breathe their final breath." Unbelievably, the former WWF Champion died the very next day.

A lot happened during the July 9, 2001 episode of Raw. Many former stars of ECW, led by Paul Heyman, declared war on the feuding WWF and WCW groups. Vince and Shane McMahon agreed to have their promotions battle the ECW faction that night, only to have WCW join ECW in a group known as The Alliance. 

Almost exactly a decade after his aforementioned debut, Brock Lesnar showed up during the final segment of the April 2, 2012 edition of Raw. Returning from a WWE hiatus that included a leading role in the UFC, Lesnar reasserted his dominance by attacking John Cena.

WWE Hall of Famer Mike Tyson showed up on the March 2, 1998 edition of Raw and exchanged some choice words with D-Generation X leader Shawn Michaels. Just as it looked like they were about to come to blows, the two embraced as Iron Mike signaled his allegiance to DX. 

After shocking the world at Elimination Chamber, John Cena appeared on the March 17, 2025 edition of Raw and seemingly erased decades of goodwill in one promo. Cena angrily explained that for his entire career, he had been in an "abusive relationship" with WWE fans.

During the April 7, 2014 edition of Raw, Divas Champion AJ Lee was cutting a promo about the lack of competiton on the roster. This prompted NXT Women's Champion Paige to come out and the two competed for Lee's championship -- which Paige won in her main roster debut.

During an unusual Thursday edition of Raw on February 13, 1997, WWF World Champion Shawn Michaels reliquinshed the championship. Instead of revealing an injury, The Heartbreak Kid said he was going home because he "lost his smile."

Randy Orton had just become World Champion the previous night and was celebrating with Evolution teammates on the August 24, 2004 edition of Raw. But leader Triple H gave Orton "thumbs down," signaling Evolution to attack The Legend Killer and turn against him.

More than a decade after he was "screwed" out of the WWF Championship, WWE Hall of Famer Bret Hart returned to Raw on January 4, 2010. The Hitman used this opportunity to finally reconcile with Shawn Michaels.

After Cody Rhodes exercised his Royal Rumble win to challenge Roman Reigns for the WWE Championship at WrestleMania, Reigns' cousin The Rock took exception to that. Outside in a rainy parking lot on March 25, 2024, The Great One bloodied Rhodes and whipped him repeatedly with a weightlifting belt.

During the July 15, 2002 edition of Raw. Vince McMahon named the program's new General Manager - WWE Hall of Famer Eric Bischoff. Given Bischoff's contentious relationship with the promotion during the Monday Night Wars, this appearance was shocking.

(well... for the first time, anyways) After losing to Shawn Michaels in the previous night's WrestleMania, the March 31, 2008 Raw was dedicated to WWE Hall of Famer Ric Flair, who retired in front dozens of his greatest friends and rivals, as well as the full WWE roster.

WWE Hall of Famers The Undertaker and Kane were about to learn which one of them was being awarded the WWF Championship by Mr. McMahon on September 28, 1999, when Stone Cold Steve Austin interrupted the proceedings by driving a zamboni to the ring.

WWE Hall of Famer Bill Goldberg was one of the few top WCW talents that had never competed in a WWE ring. That changed on March 31, 2003, when Goldberg arrived in the main event spot and speared The Rock, signaling he had arrived.

The February 18, 2002 edition of Raw was highlighted by an in-ring segment with The Rock and WWE Hall of Famer Hollywood Hulk Hogan. The two icons traded stares, boasts and insults before Rock challenged Hogan to a match at that year's WrestleMania.

One of the turning points in the Monday Night War happened on April 27, 1998. In a pre-recorded segment, WWE Hall of Famers D-Generation X "invaded" a nearby WCW Nitro show, dressing in military fatigues and driving a Jeep, declaring war on the rival company.

WWE Hall of Famer Edge decided to commemorate his first WWE Championship on January 9, 2006 by having a "live sex celebration" in the ring with his girlfriend Lita. The risqué segment featured a bed in the center ring, and interference from Ric Flair and John Cena.

After WWE Hall of Famer Shawn Michaels lost the WWF Championship at WrestleMania, fellow D-Generation X member Triple H kicked The Heartbreak Kid out of the group on the March 30, 1998 Raw. He immediately added X-Pac and The New Age Outlaws to the group.

The day the World Wrestling Federation acquired World Championship Wrestling, both WWF Raw and WCW Nitro featured a live simulcast on March 26, 2001. The final segment on both shows featured Shane and Vince McMahon fighting over the ownership of WCW.

Most WWE weddings end in chaos and disaster, and arguably the best example of that happened on November 29, 1999. Test was set to marry his fiancee Stephanie McMahon, but the marriage was.. well, disqualified, because Triple H had married Stephanie the previous night.

Following the shocking results at the 1997 Survivor Series (perhaps you've heard about it?) the November 17, 1997 Raw featured an out-of-character interview with Vince McMahon. Speaking with WWE Hall of Famer Jim Ross, McMahon coldly stated that "Bret screwed Bret."

For months, fans were waiting for WWE Hall of Famer Stone Cold Steve Austin to deliver his Stone Cold Stunner to company owner Vince McMahon after he did so to other authority figures. That moment finally happened on the September 22, 1997 Raw, with the Madison Square Garden crowd erupting in cheers.

The January 4, 1999 edition of Raw was a pre-taped show and was expected to lose in the ratings to Monday Nitro. However, WCW spoiled the result that WWE Hall of Famer Mick Foley (a/k/a Mankind) was going to win the WWF World Title. Fans immediately tuned from Nitro into Raw to watch the title change.

Arguably the biggest debut in WWE history took place on the August 9, 1999 edition of Raw. Chris Jericho, who had previously worked in WCW, interrupted The Rock and cut a legendary promo on his arrival, instantly giving Jericho credibility and the status of being a top star.

Kane was feuding with fellow WWE Hall of Famer Triple H, and their final encounter in the rivalry on June 23, 2003 forced The Big Red Machine to unmask. While Kane's face wasn't scarred from a childhood fire (which we had been told was the case), he did sport a gruesome and eerie look underneath the mask.

The Netflix debut of Raw on January 6, 2025 had a main event that was worthy of headlining the first episode on the worldwide streaming service. CM Punk defeated Seth Freaking Rollins in a match that literally had years of bad blood brewing the two competitors.

One of the most impressive debuts in Raw history happened on March 18, 2002. During a Hardcore Match between Maven and Al Snow, Brock Lesnar showed up and destroyed both men. He also attacked Spike Dudley, delivering several powerbombs to the performer, and then showing his allegiance to Paul Heyman.

Fresh off of receiving their unexpected releases from WCW, wrestlers Eddie Guerrero, Chris Benoit, Dean Malenko and Perry Saturn showed up in the front row of the January 31, 2000 edition of Raw. They very quickly become involved in the action as The Radicalz.

On the March 24, 1997 edition of Raw, WWE Hall of Famer Bret Hart explained his recent heelish actions to the audience. The Hitman said he apologized to his fans around the world, but that the American wrestling fans could "kiss my ass."

The June 7, 2010 edition of Raw concluded in a very violent way. Following a match between John Cena and CM Punk, Wade Barrett and the rest of the NXT Season One participants invaded the ring, destroying Cena and literally tearing apart the entire ringside area to debut as The Nexus.

For several weeks, The Corporate Ministry spoke of a "Higher Power" that would help the Shane McMahon and Undertaker-led faction rid the WWF of Stone Cold Steve Austin. A hooded figure showed up on June 7, 1999 and revealed The Higher Power to be Mr. McMahon.

The Shield (Seth Rollins, Dean Ambrose and Roman Reigns) had just defeated Triple H's Evolution the evening before when The Game revealed his "Plan B" on June 2, 2014. It featured Rollins turning on his partners and joining Triple H.

Five months after Evolution dropped Randy Orton, Batista was faced with a decision: face his partner Triple H at WrestleMania or face SmackDown's JBL instead. On the February 21, 2005 edition of Raw, Batista gave the "thumbs down" signal and attacked Triple H.

WWE Hall of Famer Stone Cold Steve Austin faced overwhelming odds every time he was against Vince McMahon and his Corporation. On March 22, 1999, Austin drove a truck to ringside and doused the heels with a hose full of beer. 

WWE Hall of Famer Mick Foley had been largely known to Raw fans as the deranged Mankind when he had a sit-down interview with Jim Ross that concluded on June 9, 1997. Mankind revealed his teenage dream to become Dude Love, which soon became Foley's third in-ring persona.

With WCW out of the way, WWE decided to create its own competition in the form of competing rosters on Raw and SmackDown. During the first "Brand Extension" on March 18, 2002, General Managers Vince McMahon and Ric Flair drafted their own talent rosters.

To celebrate the 10 year anniversary of The New Day, the December 2, 2024 Raw featured a reunion of sorts between members Big E, Kofi Kingston and Xavier Woods. However, Kingston and Woods shockingly turned heel on Big E, signaling the team's move from a trio to a duo.

The December 6, 2004 edition of Raw was headlined by WWE Women's Champion Trish Stratus defending her title against fellow WWE Hall of Famer Lita. Not only was this the first time women held the main event spot of Raw, but Lita also captured the championship.

For nearly a year, WWE Hall of Famer Triple H was out of action with a quad tear. His return on the January 7, 2002 edition of Raw featured The Game declaring himself for that year's Royal Rumble, with an extremely loud reception from the Madison Square Garden crowd.

Chris Jericho and Kevin Owens had presented themselves as best friends leading up to their Festival of Friendship on the February 13, 2017 edition of Raw. What started as an over-the-top segment ended with Owens turning on Jericho and ambushing him.

The annual drafts between Raw and SmackDown talent made sure each show's roster was freshened up. Nowhere did that make a bigger splash than on the June 6, 2005 edition of Raw, when WWE Champion John Cena was drafted from SmackDown to Raw.

One of the most unconventional segments in the history of Raw took place on September 27, 1999, when WWE Hall of Famer Mick Foley presented his tag team partner The Rock with "This Is Your Life," complete with people from Rock's past and a clown named Yurple.

The evening after his tragic passing at a WWF pay-per-view, the company presented a tribute show to the late Owen Hart on May 24, 1999. The episode featured videos from Hart's career, non-competitive matches and emotional tributes from many of his peers.

One of the biggest upsets in wrestling history happened on the May 17, 1993 edition of Raw. WWE Hall of Famer Razor Ramon was battling the previously-unheralded 123 Kid in a squash match, but the future WWE Hall of Famer pinned Ramon in a shocking twist. 

On the October 5, 1998 edition of Raw, Mr. McMahon was convolescing in a hospital due to injuries at the hands of WWE Hall of Famer Stone Cold Steve Austin. Austin disguised himself as a doctor to get into the hospital room and attacked the Chairman with a bedpan.

One of the most controversial segments in wrestling history happened on the November 4, 1996 Raw. While at his home nursing an injury, Brian Pillman protected himself from a Stone Cold Steve Austin home invasion by brandishing a gun and threatening to use it.

Two of the biggest, toughest names in combat sports met in the ring on the January 19, 1998 edition of Raw. WWE Hall of Famers Stone Cold Steve Austin and Mike Tyson exchanged heated words and had a pull-apart confrontation, all while Vince McMahon was fuming that the segment had been "ruined."

The final segment on the June 27, 2011 edition of Raw saw WWE blur the lines between reality and fiction. CM Punk, who hadn't re-signed his WWE contract, cut a scathing promo on the company and Vince McMahon, making references to things that were never uttered before on WWE television.

Although many of the entries on this list feature a variant of WWE Hall of Famer Stone Cold Steve Austin battling Vince McMahon, their first actual match on the April 13, 1998 edition of Raw is easily the show's biggest moment. Not only did this segment solidify Austin's role as a wrestling icon, but it also turned the tide in the Monday Night Wars, helping the WWF soundly defeat WCW.