Monday Night Raw has been the flagship show of WWE for three decades and has showcased numerous iconic moments in WWE history. Some wrestlers made their careers competing in the show, and it is running successfully after crossing over 1550 episodes as of this date.
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Apart from the high-octane wrestling action, Monday Night Raw has also shown some of the best segments. Some of these are comedic gold and would give the fans a good laugh even today. With that said, let's take a trip down memory lane and look at ten of the funniest moments in Monday Night Raw history.
10 R-Truth & Drake Maverick's 24/7 Championship Segments
The now-retired 24/7 Championship had a good run and decent screen time during its initial days in WWE, and R-Truth and Drake Maverick were two wrestlers who became a vital part of the title storylines.
They traded the title with each other on many occasions and put on some of the funniest segments in the history of WWE. Segments like R-Truth crashing Maverick's wedding and interrupting Maverick and his wife, Rene Michelle, consummating their wedding at their hotel room are some of the best comedic angles WWE produced in many years.
9 Santino Marella's Tea Party With Sheamus
Santino Marella is one of the best WWE superstars who have the natural ability to give the fans a peal of good laughter. Marella has been part of numerous hilarious segments over the years, and his tea party segment with Sheamus and Vladimir Kozlov remains one of his best works.
The segment took place on the November 8, 2010, episode of Raw, and Marella's hilarious antics proved too much for Sheamus as he was caught struggling to hold back his laughter on live television.
8 Brock Party
Ever since he returned to WWE in 2012, Brock Lesnar continued to portray a serious monster heel persona who just looked to destroy his opponents. However, with a person having more creative control over his character, Brock Lesnar has gone out of his way to break character or show different versions of his character, and he introduced the fans to one such version after he won the Money in the Bank ladder match in 2019.
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He converted the MITB briefcase to look like a boombox, and when he walked out to the ring to confront WWE and Universal Champions Kofi Kingston and Seth Rollins on the May 27, 2019, episode of Raw, he even ripped out some dance moves much to the surprise of the fans and the wrestlers standing in the ring.
7 Kane and Daniel Bryan's Anger Management Segments
The start of Kane and Daniel Bryan's Team Hell No storyline saw Raw General Manager AJ Lee send them both to anger management therapy. The segments in which both Kane and Bryan undergo therapy under Dr. Shelby were some of the best comedic skits WWE produced.
Segments like the one in which Kane shares his childhood story with the group, the trust fall, the restaurant, the hugging it out, and the live graduation turned out to be comedic gold, and they made the fans burst out in laughter every single time.
6 Vel Venis and The Big Show's GTV Segment
WWE used to air the GTV segments back in 1999, which saw the wrestlers getting caught doing some hilarious stuff in hidden cameras placed all over the arena.
One such segment saw Val Venis and The Big Show relieving themselves in the men's room on the September 6, 1999, episode of Raw. The segment saw Val Venis peeking into The Big Show's privates before bursting out in laughter and saying, "And they call you The Big Show."
The Big Show didn't take too kindly to Venis' gesture and slammed him onto the wall before walking away.
5 DX Impersonate The McMahons
After Triple H and Shawn Michaels reunited and reformed D-Generation X as a tag team during their feud against the McMahon family in 2006, The Game and HBK made it their personal mission to humiliate Vince and Shane McMahon through various hilarious segments.
One such segment took place on the June 26, 2006, episode of Raw, where Triple H and Shawn Michaels impersonated Vince and Shane McMahon respectively, and hilariously took shots at their rivals.
Triple H did his Vince McMahon impression to perfection and Shawn Michaels followed it up with his own act as Shane McMahon, and the fans had a good laugh with DX's antics from the segment.
4 Stone Cold Attacks Mr. McMahon In The Hospital
Stone Cold Steve Austin was the biggest rival of the McMahon family as the Texas Rattlesnake gave Vince McMahon a tough time during their infamous rivalry between 1998 and 1999 and made the boss' life a living hell.
Austin jumped on any opportunity to get one over on McMahon during the feud, and a segment on the October 5, 1998, episode of Raw, saw Austin go to great measures to disguise himself as a doctor and attacked Vince McMahon who was in a hospital bed.
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Austin hilariously attacked McMahon's injured leg, and the sound of the Texas Rattlesnake hitting McMahon with a bedpan can still be heard among WWE fans.
3 Booker T & Goldust Segments
After getting kicked out of the nWo in 2002, Booker T formed a partnership with Goldust, which led to a series of hilarious segments between the two throughout their partnership.
Goldust was the one who tried to form a partnership with the 5-time WCW World Heavyweight Champion, but Booker T wouldn't give in until he got betrayed by the nWo. Following their team-up, Goldust and Booker T put on various hilarious backstage segments, including the one in which Goldust dressed up s Darth Vader, which ended with Booker T hilariously playing with the lightsaber.
2 MilkOMania
Wrestling fans witnessed the iconic segment in which Stone Cold Steve Austin brought a beer truck to douse the Corporation with a beer bath. But the Texas Rattlesnake got a taste of his own medicine when Kurt Angle recreated the segment with a twist when he brought a milk truck on the August 20, 2001, episode of Raw.
While Austin was in the middle of the segment with the rest of the Alliance, Angle drove a milk truck to ringside and doused everyone with a milk bath, and the fans enjoyed the moment with some loud cheers.
1 The Rock, This Is Your Life
The Rock formed the Rock 'n' Sock Connection tag team alongside Mankind back in 1999, which gave the fans lots of hilarious segments between the two legendary superstars throughout their alliance.
One such angle was the iconic "This is Your Life" segment Mankind put together for The Rock on the September 27, 1999, episode of Raw. Mankind brought in characters from The Rock's past to the ring, only for the latter to berate them.
It became one of the most popular segments in WWE history and helped Raw get a excellent television rating, and still remains one of the classic examples of The Rock and Mankind's work in their prime.
