Skip Bayless' Most Hilarious Moments

Skip Bayless recently signed a four-year deal with Fox Sports worth $32 million. This deal will keep him on Undisputed, the debate show he hosts alongside Shannon Sharpe. The two have shown great chemistry over the years and while fans love them as co-hosts, there are still some people out there who were hoping that Bayless would finally come back to ESPN and be reunited with Stephen A. Smith, with whom he had a phenomenal rapport.

Regardless, Bayless remains a massive part of the sports television landscape and even if you vehemently hate his sports takes, you still have to admit that he is one of the most entertaining men when it comes to his opinions. With that being said, we decided to look back on Skip’s career and bring you some of the times in which he had us laughing the hardest, whether he meant to garner that response, or not.

Skip Does The Dougie

Skip Bayless has never been shy about making a fool out of himself, and that is exactly what he did back in the day on First Take, during the height of the “Dougie” craze. John Wall used to do the dance before every single game and after one of his performances went viral, Skip felt the need to give the dance his very own shot. As you can imagine, it was a hilarious mess, all while Jemele Hill couldn’t help but crack a smile at Skip’s embarrassing moment. It’s one of the moments that defines who Bayless is as a broadcaster, which makes it the perfect clip to start off the list.

Skip Dresses Up Like LeBron And Poses With A Brick

Throughout his career, Skip has been one of the most staunch critics of LeBron James. No matter how well LeBron is doing out on the court, you can be sure that Skip is going to have something extremely negative to say about it. This far into his career, Skip won’t be changing anytime soon, although there have been some instances where his hate led to a funny moment. Case in point, the time when Bayless went on ESPN’s First Take and dressed up in a LeBron Cavaliers jersey while posing with a brick as if to say that LeBron can never hit big shots. LeBron’s lack of ability in the clutch is a narrative Bayless has been pushing for decades, and this moment was the pinnacle of it. Of course, there was some creativity to be had here, which is what made it so goofy.

Skip Throws His Ezekiel Elliott Jersey In The Trash

Skip might be 69 years old but that has never stopped the man from acting like a huge baby. When Skip doesn’t like something, he will typically sulk about it, especially if it has to do with one of the teams he supports. The best example of this is the Dallas Cowboys, who have disappointed Bayless on numerous occasions. The broadcaster has had a love-hate relationship with the team’s running back, Ezekiel Elliott, in particular. After a string of bad games in the midst of the 2019 season, Bayless got a little too angry on a Sunday afternoon and decided to throw his Elliott jersey right in the trash, only to take it out a few hours later. The moment was obviously staged, although it was one of those Skip tantrums that you couldn’t help but laugh at. If you ever needed confirmation that Skip is just a troll, this was it.

Skip Officially Co-Signs The Drip Bayless Nickname

Every few days, before an episode of Undisputed, Skip takes to his Instagram account and posts the Jordans he is wearing before the show. The caption is always the standard “I can’t lose in these shoes” and fans always look to critique him on his choices. Bayless is unashamed when it comes to Jordans and whether it be rare Jordan 1s or some Team Jordans, he is always ready and willing to rep the Jumpman logo. Not to mention, Bayless’ suit game is always on point and his chain from Lil Wayne has had many fans refer to him as Drip Bayless. Just a couple of years ago, Bayless caught wind of the nickname and officially embraced it in front of Shannon Sharpe, leading to a hilarious moment between the two as Sharpe couldn’t help but laugh. The social media reaction to it was intense, and once again, Skip has us smirking, if only as a slight distraction from his atrocious takes.

Skip Goes Too Far With His Tim Tebow Love

When Tim Tebow burst onto the NFL scene with the Denver Broncos almost a decade ago, Skip could not contain himself. In fact, Bayless used to go just a bit too far with his Tebow praise, sometimes, bordering on pure insanity. Bayless’ most hilarious Tim Tebow moment came in the midst of Tebow Mania when the quarterback was winning all of those games in the clutch. Bayless went so far as to claim that Tebow was a better clutch quarterback than Tom Brady, which nearly had Stephen A. Smith on the floor. A few months later, Bayless claimed that Tebow should actually be making more money than the likes of Kobe Bryant and LeBron James, which forced Smith to walk off the set. It was easily one of Bayless’s most hilarious string of hot takes, and it gave us a ton of laughs.

Skip Claims Scottie Pippen Isn’t A Top 50 Player All-Time

Who can forget the time Stephen A. straight up told Skip “you don’t know the game of basketball, you just got caught.” Well, if you forget why Smith said that, it was because Bayless tried to claim that Scottie Pippen was not a Top 50 player in the history of the NBA. In the clip above, Bayless tries to say that Michael Jordan simply brought Scottie along for the ride and that when Pippen left for the Houston Rockets, he was never the same. Bayless even asserts that Pippen was in his prime at the time, which is simply not true. His takes enrage Smith, and that’s when we get one of the best First Take moments of all-time. Sure, we’re laughing at Skip’s expense, but it counts.

Skip Gets Called Out By Jalen Rose

“Water Pistol Pete Jr.” is the nickname that First Take fans will always remember. Of course, this is because of Jalen Rose, who went scorched earth on Bayless back in the day following a heated debate in which Skip questioned Rose’s place in the NBA. Rose also pointed out that Bayless only averaged 1.4 points per game during his high school basketball career, which is something that had TV audiences in stitches over. Once again, it’s a moment where Bayless is the subject of the laughter, but alas, here we are. Not to mention, the 30-minute debate that happened the day after, was just as hilarious, with Stephen A. Smith backing up Bayless as if he was a lawyer and Skip was the defendent.

Skip Finally Forgives Kawhi Leonard

Skip Bayless is a huge San Antonio Spurs fan so it shouldn’t be a surprise that Bayless was hurt when Kawhi Leonard forced his way out of the city. During his championship run with the Toronto Raptors, Bayless was the biggest hater around, and wouldn’t even acknowledge Leonard by name. Eventually, however, Kawhi signed with the Los Angeles Clippers who were the main rivals to Skip’s least favorite player, LeBron. This led to an Undisputed Halloween special in which Skip dressed up like Kawhi and reclaimed his fandom of The Klaw, once and for all. It was a truly pathetic move but the exasperated “What it do Baby” makes this one of our favorite Skip moments, just because of the sheer ridiculousness of it all.

What are your favorite Skip Bayless moments? Let us know, in the comments below.