The Shady Side Of Scott Disick

Let's be honest: the men the Kardashian-Jenners date have it made. Would Travis Scott have a No. 1 hit without his self-made billionaire baby mama, Kylie Jenner? Khloé Kardashian is still supporting ex Lamar Odom after his 2015 overdose. And somehow, Scott Disick basically gets to ride around on private planes for being the on-and-off boyfriend of Kourtney Kadashian. Perhaps, Disick — who's not a rapper or professional athlete and has few discernible talents beyond professional-level trolling — achieved the biggest feat of all. He's seemingly famous for absolutely nothing.

Fans of Keeping Up with the Kardashians will admit that Disick is one of the best, most awful characters on the reality show. He's continuously stirring up drama while not doing a whole lot of anything else (seriously, what does he do?). Yet, the famed family have basically adopted him like a lost child, who's in charge of watching three children of his own. 

In many ways, Disick is somewhat of a Kardashian enigma. He's a chosen member of one of the most famous families on the planet, but doesn't even have a Wikipedia page. He's managed to finagle his way into everything from reality shows to royalty, leaving audiences absolutely bewildered that he's achieved such massive success. Grab your fashion cane, and let's take a deep dive into Scott Disick's shady side.

Scott Disick has a huge preoccupation with Kourtney Kardashian's weight. Using little jokes and snipes — despite the fact that tip No. 4 of his "Six Tips to Living Like a Lord" is "Be Direct" — he constantly mentions her weight, especially when she is pregnant or has recently birthed one of his babies. (Does he know how the female body works?)

One of his worst weight gain-related remarks, of the many, many to choose from, was when he basically told Kourtney she should always weigh as much as when they first met. "If I would have fallen in love with you a couple pounds overweight, this would be my ideal weight. But I fell in love with you when you were super skinny, so..." he once said. Disick also concluded that "93 [pounds] is the dream," even though that would make Kardashian, who's 5 feet tall, underweight.

The media has a constant obsession with the size of the Kardashians' derrieres. The Guardian even claimed Kim Kardashian "broke the Internet with her butt." Sister Kourtney certainly doesn't need to hear these comments when she gets home, too. They're more than enough justification to kick Disick to the curb, even without considering the additional avalanche of shade that is his life. What exactly does that entail? We're glad you asked.

Having a drinking problem is no joke, and being an alcoholic certainly doesn't make you shady. However, if you repeatedly fall off the wagon while promising your on-and-off girlfriend and mother of your three children that you're getting your act together, only to reportedly never really try to commit to it, then guess what? Welcome to Shadesville.

Scott Disick has a habit of using rehab like a revolving door — the Lord cometh, and the Lord goeth. In January 2016, the reality star reportedly bailed on a fourth rehab stint, according to Radar Online. Later that month, he allegedly overdosed on a mix of "booze, cocaine and Viagra," but was revived with an adrenaline shot, according to Life & Style (via Radar Online). By the summer of 2017, the star was reportedly so out of control that he was allegedly hospitalized and placed in a 5150 psychiatric hold. The Sun reports that he was kicked off Keeping Up with the Kardashians shortly thereafter due to his hard-partying ways and refusal to enter rehab.

Disick previously tried out rehab in 2014 and twice in 2015, according to E! News. He cut his stays short every time. At this point, if Disick heads back to detox for the fifth, sixth, or even seventh time, is it realistic to hope that he'll be able to stay clean?

In a 2013 Haute Living interview, Disick described his typical day. He generally wakes at 10 a.m., then takes three hours to shower and select his clothes, shoes, wristwatch, and car for the day. Once properly accessorized, he spends a grueling five hours telecommuting for his "job," which he describes as: "The truth is I work in various industries. I have done a lot of private label manufacturing in the nutrition biz and have raised money for startup companies. I tend to invest money into nightlife businesses the friends of mine that are involved in nightclubs and what not."

In reality, the Disick family fortune was made by Scott's grandfather, David M. Disick, an attorney-turned-real estate developer who pioneered the development of luxury ski resort communities, according to Starcasm. So try to guess where Scott's "private label manufacturing" and nightclub investment capital likely came from.

Of course, Disick now makes serious money from KUWTK and its various spin-offs — a reported $4 million per year, according to TMZ, not to mention up to $100,000 a pop for those infamous club appearances. All of this is to say that his entire livelihood depends on keeping his arguably toxic relationship with Kourtney on the air, as well as partying nightly in Vegas clubs, which is not exactly ideal for someone who struggles with substance abuse.

This is far from the shadiest thing Scott Disick has ever done, but it's worth mentioning because it speaks to what an inflated sense of self-worth this guy appears to have. According to TMZ, Disick demanded a $500,000 fee to appear on Season 22 of Dancing with the Stars. That's far more than what the show was reportedly offering, which was a "$125k guarantee and if he made it to the finals he'd get $345k."

Sure, he could have easily made that money getting hammered in a Las Vegas nightclub over a long weekend, but still, who does this guy think he is? Let's look at the facts: Billy Dee Williams did a Star Wars themed cha-cha for way under half a mil. According to Variety, even Sean Spicer, the former White House Press Secretary, only stands to make a maximum of $295,000 from the series in 2019. Plus, he had to trade in his boxy, oversized suit for a lime green, ruffled get-up that — as The Daily Beast pointed out — "evoked Big Bird." 

If Spicy, who arguably held one of the government's most prestigious positions, was willing to embarrass himself on live TV for less than half a million dollars, the Lord isn't worth anywhere near the holy water he bathes in.

The only thing shadier than Scott Disick constantly referring to himself as Lord is the fact that he actually found a loophole to literally become a Lord without actually doing anything at all. According to Us Weekly, Disick was absolutely obsessed with becoming British royalty during a trip to London that was featured on Keeping Up with the Kardashians. Instead of waiting 36 years to meet his prince like Meghan Markle, the reality star fast-tracked his ticket to the top by purchasing the title on the Internet and having an authentic knighting ceremony. He still hasn't been given keys to the castle (or Buckingham Palace), but he has made his fake knighthood an entire brand.

Beyond annoying the cast of KUWTK by walking around with a cane, he bought velvet slippers with his Lord moniker and snatched up the Instagram handle @letthelordbewithyou. He even had a now-defunct web series called Lifestyles of a Lord, a send-up of Lifestyles of the Rich and Famous, only instead of profiling many wealthy people, the show was entirely about him. 

Sadly, Disick's cultural impact is pretty much limited to private plane selfies and weight loss tea ads. He doesn't even have a Wikipedia page (probably because Kris Jenner would be horrified with what it says). Sir Paul McCartney, Sir Elton John, Sir Scott Disick. Yeah, those names absolutely make sense together. When even Rob Kardashian thinks "it's kind of weird," you know it's bad.

Disick told Haute Living that "the biggest choice of the day is the wristwatch." He wears lavish fur coats, despite not actually being Cruella De Vil or Conor McGregor. His everyday runaround car is his Bentley Mulsanne, for when he just doesn't feel like getting out the Rolls. His Instagrams are nothing but private jets, luxury cars, and designer clothes. Oh yeah, his kids occasionally make an appearance, too — if they can squeeze into the shot with the Lambo. We get it, Lord, you're doing quite well.

On top of all of that, Disick once flaunted his wealth in the most objectively awful way — by being horrendously rude to a waiter. After getting belligerently drunk, Disick got cut off by a waiter — at Kris Jenner's request, according to People — at which point he became enraged and "attempted to shove a $100 bill in the waiter's mouth." And did Lord Disick feel remorse for his King Joffrey-esque behavior?

Hardly. "Kourtney knew exactly who she was with when she met me," Disick reportedly told Kim Kardashian. "And I will never take back the things that I do, or why I do them. The guy disrespected me."

You know that rule about how you can tell a person's true nature by the way they treat service professionals? Yeah...

After that arduous, hours-long rehab stint in July 2015, Scott Disick reportedly ran straight into the arms of an ex-girlfriend and chose to party in Monte Carlo instead of spending the Fourth of July with his family, according to TMZ. Though this was the first time real photo evidence of a blatant PDA was available, it was apparently the last straw for Kourtney Kardashian, who at the time of this writing, has not taken him back.

Prior to getting caught red-handed, reports that Disick cheats have been frequent. Almost every time he goes out of town for a public appearance, sources later claim Disick acted on his wandering eye. Granted, it's not unusual for tabloids to make this kind of thing up, but historically speaking, men who consider themselves "Lords" don't necessarily consider monogamy a virtue.

Scott Disick has three kids with Kourtney Kardashian: Mason, Penelope, and Reign. After allegedly ditching them all sometime in late-June 2015 to party in Europe, Disick supposedly still chose to stay away when he returned to the States and instead called for periodic updates. He even missed Penelope's birthday, but no biggie, because he fired off this since-deleted message to her on Instagram: "1 of the only things I'm proud off about myself. Happybdayp."

Three-year-olds are on Instagram and have the mental capacity to read, right? Eh, whatever. And then there's this tidbit: one of the only things he's proud of? He has two other children. Not that he's made a colossal effort to see them, either. According to People, Disick reportedly duplicated his 2015 disappearing act again in the summer of 2017, with sources telling the magazine, "The kids hadn't seen him for weeks and really missed him."

Supposedly, Disick is now keeping a low profile and "spends his nights at home" with his adorable kiddos, but even Kourtney was dubious of the supposedly turned-over leaf. "Kourtney is still not happy with Scott, but that's not the focus for her," a source told People, adding, "She wants the kids to have the best relationship with their dad so that's her focus."

Good luck with that.

What's the worst possible way to get back into the good graces of your estranged ex-girlfriend? If you guessed "by going on vacation with her sister then inviting some random girl back to your hotel room," you win! That's exactly what Scott Disick did during Kim Kardashian's Dubai trip (which he tagged along on for some strange reason).

According to E! News, Kim acted in surrogate outrage for her sister when she confronted Disick's mystery lady, who had locked herself in the bathroom. "What the f**k are you doing here?" Kim reportedly said, before politely suggesting the young lady exit the premises. "Seriously? You're just like a f**king whore. Such a tramp. Get your s**t and get the f**k out of here. F**king groupie. Get your s**t and security will escort you the f**k out of here!"

Kourtney responded by allegedly disinviting then reinviting Disick to the family's upcoming Costa Rica trip, and you'll never guess what happened next...

Yes, that's right, Disick apparently doubled-down when he showed up for the Kardashian-Jenner family's January 2017 Costa Rica trip with an uninvited plus one. With the ordeal being portrayed on an episode of Keeping Up with the Kardashians, the needle on the shade-o-meter started moving when Disick chose to stay at a different hotel than the rest of the Kardashian crew because he couldn't "handle staying under the same roof as the love of his life when he can't sleep with her," according to The Cut. The shade darkened after Kim's assistant reported that a woman named "Chelsea" was staying at Disick's place, which the sisters dealt with by throwing water in his face, then continuing to hang out with him the entire trip.

In fairness, a later scene portrayed Kourtney coolly informing Disick that she'd reached her limit with his shenanigans and there would be no reconciliation. Disick, who had previously and repeatedly professed that Kourtney was still the love of his life, reacted accordingly, which is to say he acted like he was perfectly fine with it. His actions a few months after the Costa Rica trip, however, spoke much louder than words.

After several months of understandable estrangement following the Costa Rica trip, Disick jetted off to the Cannes Film Festival with then-19-year-old former Disney starlet Bella Thorne on his arm. After a few days, she reportedly got burned out on his hardcore partying and split, at which point Disick paraded a steady string of blogger/model/social media stars in front of the paparazzi. According to E! News, this list included Chloe Bartoli, the ex from his 2015 European romp that effectively ended his relationship with Kourtney for good. Nope, this didn't sound like petty revenge at all.

Keep in mind this wasn't the first time Disick's did the model shuffle for the paps. Back in February 2017, hot off the heels of his Costa Rica performance, Disick was spotted in Miami partying with multiple young "mystery ladies," according to E! News.

But back to Cannes, where Disick's string of day dates ended with 18-year-old Sofia Richie, who partied with him on a yacht but denied any romance by tweeting: "Just so everyone can get their panties out of their a**es, Scott and I are just homies #relax." But it would seem the lady has protested too much, because...

As of this writing, Scott Disick and Sofia Richie are officially a couple in spite of their 15-year age difference and the fact that he can't seem to walk outside without tripping over several random women in bikinis who are dying to "party" with him. But we're not here to judge.

It wouldn't necessarily be all that shady for Disick to be hooking up with Richie if it wasn't for the fact that she dated Justin Bieber, who's been previously linked to Kourtney, making this whole thing once again seem like a revenge-fueled plot by the Lord of Shade. Of course, that's all pure speculation, but he did wind up taking Richie on a family vacation with Kourtney, as depicted in a 2019 episode of KUWTK. He reportedly called the family vacation a "really awkward situation," while Kourtney claimed she thought it was "bizarre."

We hope, for Richie's sake, that Disick has finally gotten his act together and will do right by her (and avoid inviting random women back to his hotel room during his holiday). However, we have to say that we share the sentiment held by her famous dad, Lionel Richie, who told Us Weekly of his daughter's new beau: "I'm scared to death, are you kidding me?"

Lord Disick isn't just the duke of nightlife. He's also the king of trolling in real-life and is so fully committed to his hard-partying lifestyle that he reportedly named his third child, Reign Aston Disick, after a nightclub. He's going to seriously have to explain that to baby Reign once he's old enough to understand that his father makes ill-advised decisions (a little more than occasionally).

According to Radar Online, Disick reportedly came up with the name in February 2014 after spending a night out in Seattle at Aston Manor. A source cited by the gossip rag claimed that he was hard partying "like he normally does" and talking to the managers and server. At the end of the night, he allegedly went back to his hotel with some of the staff, where they reportedly got drunk and started prank calling people at four in the morning. Before that, Disick reportedly told them, "Aston, I love that name. I'm going to name my son Aston." 

For some reason, Kourtney Kardashian went along with it. After all, it is the word of the Lord.

Sofia Richie is finally old enough to legally join Scott Disick on his wild nights out; however, it appears like the Lord is still thinking about his ex. Even though Kourtney Kardashian allegedly rejected his marriage proposal during their 2017 family vacation to Costa Rica, he still wanted to add another child to their brood.

In a 2019 episode of Keeping Up with the Kardashians, it was revealed that Disick texted Kim Kardashian to say he wanted to have another baby with Kourtney — not Richie, his current girlfriend as of this writing, but maybe not his current girlfriend once she watches the episode. "With Kourtney ... I think he just wants one more. And she wants one more," Kim said. "I mean, it's like Scott has a girlfriend, Kourtney has a boyfriend, we get it, so they don't even have to have sex. It can be like IVF."

Try explaining that to your 21-year-old girlfriend, boo.

It's not clear who Scott Disick was throwing shade at with his fashion brand, but it looks like he might have been trolling himself. In 2018, the reality star — who essentially makes a ton of money doing, well, no one's quite sure — launched Talentless, a vessel to hawk $52 plain t-shirts and $119 plain hoodies. It's not quite Yeezy money, but it's something.

Talentless is hardly Disick's first venture into retail sales. According to Page Six, the star claimed he worked for the health chain GNC, but a spokesperson clarified that he does not. He also briefly hawked supplements for male menopause and continues to regularly post #SponCon about weight loss drinks. Talentless, however, might be the most Disick of all of Disick's ventures. The Cut hailed it as the star's "best worst self-own." 

Perhaps the idea for the simple clothing line was sparked by GQ's 2016 feature on celebrity club appearances, which pegged the Lord as the Kardashian by-proxy who's "routinely mocked on national television for being the one without any skills in a family of people who are famous for not really having any skills." Maybe it refers to Disick's former manager who, according to the Mirror, basically called him a talentless "couch surfer." Either way, the brand's about page makes Disick's message clear: He's hoping to reach people who are famous for being, well, rich, beautiful, and famous.

Scott Disick's shady side might come out while he's drinking, but it seems like his younger girlfriend has helped him change his ways. According to Life & Style, Disick celebrated Sofia Richie's milestone 21st birthday in August 2019 without taking a single sip of alcohol — and it all went down in Sin City, a place notorious for heavy drinking. Disick reportedly didn't touch the hard stuff while Richie allegedly took "shot after shot at the day club." She even got a "champagne shower fire drill" ... whatever that means. "The two spoke often but Scott maintained his distance on another banquette while Sofia did shots and partied," a source told Life & Style. "... Scott was definitely letting her have her fun while he stayed off to the side and sober." 

A second report by Radar Online also gives us some hope that the Lord is reformed. His KUWTK spin-off Flip It Like Disick was reportedly withheld for two years by Kris Jenner, who wanted to make sure the star wasn't hard-partying before giving it the go-ahead. The show premiered in August 2019 after Disick allegedly "snapped out of it" and "transformed himself." During a 2019 episode of KUWTK (via Radar Online), Kim Kardashian even admitted, "It's really nice to see how much Scott has grown and how much he's invested in really being a great dad to the kids." 

There's hope for the Lord yet.