The Messiest Celebrity Entanglements Of All-Time, Pt. 1

Source: Prince Williams/WireImage

We’re on DAY 5 of the deliciously messy Entanglement era that started when embattled R&B star August Alsina revealed his spicy somethingship with Jada Pinkett Smith during his now infamous spill-all interview that stirred up all sorts of hilarious chaos across the whole entire internet.

Naturally, Jada brought herself to thee Red Table with husband Will and confirmed her, uh, “entanglement” with August on a record-shattering episode of hit Facebook Watch show “Red Table Talk” that attracted 12 million+ viewers while fueling endless buzz on social media.

According to Jada, the entangleship began shortly after they adopted August into their famed family at his lowest moment. If you recall, he was in alllll the pics, at every family gathering, enjoying life on sun-kissed vacays in paradise as their ‘dear family friend.’

A ‘dear family friend’ who looked genuinely happy in pics with Jada who was quietly separated from hubby Will who had rumored entanglements of his own.

Oh yes, it was quite the pop culture obsession that lingered online for years as one of the LEGENDARY celebrity entanglement sagas that we compiled for your early week entertainment.

Hit the flip for Part 1 of the absolute wildest, craziest and MESSIEST celebrity entanglements ever, of ALL-TIME.

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August Alsina & Jada Pinkett Smith

Will & Jada separate. Jada connects with a vulnerable August after adopting him into the family. August befriends Jada’s son and entangles with her while she’s separated. Will & Jada reconcile. Jada untangles with August. Whew chile.

Source: Jason Merritt/Getty Images / Getty

You may recall Jada hinting that Will did his own entangling during their marriage and was probably referring to his rumored fling with “Focus” co-star Margot Robbie.

Source: Richard Lautens/Toronto Star via Getty Images

Of course, Margot denied the tryst after photos of the two getting a liiiil too cozy surfaced online.

Source: Patrick McMullan/Patrick McMullan via Getty Images

Aaliyah, Dame Dash & Jay Z

Ah yes, the infamous entangleship that allegedly broke up one of the biggest, most successful dynasties in Hip-Hop: The Roc.

At the time, Dame was dating Aaliyah who also had Jay Z crazy in love

“He tried very hard,” Dame recalled in an interview with Page Six. “I did not mean to fall in love with Aaliyah, she was just that cool. But you know, we were both going hard…everybody was trying to get to Aaliyah—it was not just Jay.”

Source: Prince Williams/WireImage

Lori Harvey & Diddy

Remember when 49-year-old Diddy was spotted doing whatever he’s doing in the above pic with his son’s 22-year-old ex-boo Lori Harvey in the club WITH THAT SAME SON IN THE BUILDING.

Source: Prince Williams/WireImage

We’re still not over how everyone just rolled with these father-son shenanigans like they were normal. But, then again, rich people live by a completely different set of rules.

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Chris Brown, Rihanna & Karrueche

You may remember when Chris Brown ‘dated’ Karrueche shortly after he was charged with assaulting ‘the love of his life’ Rihanna.

We’re sure you also remember when they got back together while Chris was still ‘dating’ Karrueche who found out about their rekindling when she saw the two booed up at a nationally televised Lakers game.

But wait, it gets worse: Chris told her he was stepping outside right quick before popping up on TV in a classic dirtbag moment that pushed her into the life-fixing arms of Iyanla.

Source: Ethan Miller/Getty Images for MGM

T.I., Tiny & Floyd Mayweather

This tangled web of marital mess started with T.I.’s many, many entanglements then swerved left when Tiny danced with Floyd at Mariah Carey’s Halloween party setting the tone for T.I.’s pull up on Floyd at a Fat Burger restaurant on the Las Vegas strip in one of the most famous fights that never happened.

Source: Bertrand Rindoff Petroff/Getty Images

Kanye West & Amber Rose

The head-turning couple seemed perfect for each other until the very end which Amber blamed on Kim Kardashian in a spicy interview with Star magazine.

In it, she claimed Kim was one of the main reasons she and Kanye split and called Kim a “homewrecker.”

She also revealed that Kim had been cheating on then-boyfriend Reggie Bush with Kanye during their relationship and even texted him nude photos.

Source: Prince Williams/WireImage

Stevie J, Joseline & Mimi

Easily the greatest entangling in reality show history that we’re not sure ever really untangled. It started with co-parents Stevie and Mimi who just couldn’t get it together. Stevie fell for his artist Joseline while still involved with Mimi who often fought with Joseline.

At one point, the three attempted counseling together in a classic LHHATL moment that exploded into a punch-throwing chaos.

Stevie eventually had a daughter with Joseline who seemed to patch things up with Mimi and complete the ultimate entanglement.

Source: Jeff Kravitz/FilmMagic, Inc

Denzel Washington & Sanaa Lathan

We’ll tread lightly but loud whispers of an entangleship between Denzel & Sanaa while filming 2003 Thriller “Out Of Time” still follow the two.

Both actors denied the rumors that persisted when Denzel’s wife reportedly considered filing for divorce from the famously private legend.

Source: Taylor Hill/Getty Images for Clear Channel

Nicki Minaj, Safaree & Meek Mill

The Rap Queen and her purse-carrying assistant/hype man/security guard/boyfriend ended their 12-year relationship that we didn’t really know ended until she popped up with her next ex Meek Mill.

Safaree eventually revealed that Meek was a big reason the two split and the target of a Game diss where we learned that Meek (allegedly) snitched on Safaree by Facetiming Nicki and telling her he was with another woman.

This was the beginning of a different type of entangling between Safaree and Meek that peaked when Meek’s goons jumped Safaree in broad daylight.

Source: Evan Agostini/Liaison

Lil Kim, Faith Evans & Biggie

It’s safe to say Biggie put his wife Faith Evans through endless stress with his notoriously toxic love life during their short time together before his tragic death.

Big was a true playa forreal (like, forreal forreal) who had multiple side chicks (that included Lil Kim and Charlie Baltimore) while married to Faith who spitefully canoodled with 2pac and found herself embroiled in the messiest beef in Hip-Hop history.