Mr. Big (whose first name John) is one of Sex and the City's most controversial characters. The suave bachelor with the wicked grin dips in and out of the show's six seasons, stirring up serious feelings in Carrie Bradshaw and usually just as much trouble. His flightiness and relationship antics attract the ire of not only Carrie, but also her friends, and this makes him one of the show's least sympathetic figures.
Nonetheless, Big's arc in Sex and the City is punctuated by some undeniably tragic moments. From health scares to self-sabotage to public humiliation, the mercurial businessman experiences several issues across the series that make his happy ending with Carrie all the more satisfying.
His Medical Scares
In the Season 6 episode "The Domino Effect" - one of the show's last before Carrie meets her late-in-the-game love interest Aleksandr Petrovsky - Big returns to New York from Napa, much to Carrie's excitement. But the reason for his visit isn't a pleasant one: he's going under for a procedure to treat his heart disease.
When Carrie finds out, she's devastated, and although Big tries to keep it cool, the surgery clearly makes him nervous too. Thankfully, it turns out fine, but it still inspires a reflection on his own mortality that causes him to (temporarily) imagine a life with Carrie. The episode marks one of Big's scariest moments, but also one of his most humanizing.
His Commitment-Phobia
When Carrie and Big get to discussing threesomes in the aptly named "Three's A Crowd," Carrie is shocked to discover that he's been married once before. Her interest in this surprising development leads her to a lunch with Big's ex-wife Barbara, a successful publishing executive. While Carrie and Barbara hit it off, Carrie discovers that their marriage ended because Big cheated.
If this wasn't enough of a red flag, he sabotages his relationship with Carrie twice and cheats on Natasha (ending his second marriage just like his first one). Despite his advanced age, Big clearly lacks maturity and communication skills when it comes to relationships - and this hurts him right alongside those he hurts.
When He Gets "Big'd" By A Fashion Model
In the Season 4 episode "Belles of the Balls," the tables turn in a shocking manner for Carrie and Big, as the latter finds himself at the mercy of a callous and detached love interest. He interrupts Carrie and Aidan's bedtime routine to complain about how his girlfriend, the famous model Willow Summers, is totally unreachable and playing games with his heart - a shocking reversal of roles for the emotionally unavailable bachelor.
Seeing Big go through such relationship troubles is one of the most fascinating - and ironic - arcs on the always-witty show.
His Unhappy Marriage To Natasha
By the end of Season 2, Big and Carrie have been through two less-than-successful romances. But one of their darkest-ever moments occurs while they're split up, when Carrie runs into Big with his new 25-year-old fiancée Natasha at a Hamptons beach party.
Although their marriage seems aspirational based on its feature in the New York Times, the reality is far from it. Carrie discovers this when Big hits on her at Aidan's furniture showcase and leaves her pining voicemails (only to later take them back). Nevertheless, the two begin an explosive affair in Season 3 that leads to the dissolution of Big and Natasha's dissatisfying union. Although Big almost definitely had a huge hand in his own unhappiness, it's still a sad part of his life.
When Carrie Embarrasses Him In Front Of An Entire Restaurant
In the Season 2 episode "Ex and the City," Carrie and Big meet for a cordial lunch - as friends. Big has just returned from the trip to Paris that inspired their second breakup earlier in the season and has just started seeing someone else (or so Carrie believes).
Although their meeting gets off to a good start, things immediately turn sour when Big drops the bomb that he and Natasha are already engaged. A totally distraught Carrie causes a huge scene and essentially puts Big's whole romantic history on blast for the whole restaurant to hear. It's an epic moment that is both heartbreaking and humiliating for Big, though perhaps deserved.
His Inability To Admit That He Loves Carrie
Season 1 of Sex and the City is filled with frivolous, flirty, and funny moments, but it also contains one of the show's saddest. In the season finale, as Big prepares to whisk Carrie away on a trip to Paris, she has a moment of clarity just as she's about to enter his car.
She asks for him affirmation that he loves her and that she's "the one," and Big pretty much refuses. To Big's credit, it's certainly an oddly timed request, but Carrie is known for wearing her heart on her sleeve, and if the next 5 seasons of the show are to be believed, he's already made a unique connection with her. The fact that he isn't able to express his obvious love for her leads to their breakup right on the spot.
When He Shows Up At Aidan's Cabin
Distraught from a breakup, a desperate Big turns to Carrie for emotional support and, with her reluctant permission, shows up at Aidan's cabin in Suffern, New York. For a down-and-out Big to drag himself upstate to a cabin owned by his nemesis to be counseled by Carrie stands out as one of the prideful businessman's most pitifully sympathetic moments.
To make matters worse, the city slicker ends up getting dragged through the mud by Aidan in an outdoors brawl.
When Carrie's Jazz Musician Date Makes Him Jealous
In Season 4's "Defining Moments," Carrie and Big, long broken up, try to be friends once again. Their quest leads them to a low-key hangout at a downtown jazz club, but to both parties' surprise, Carrie attracts the attention of one of the musicians.
He and Carrie hit it off after the show, leaving Big in the deliciously awkward position of third wheel. The brooding bachelor is clearly resentful of Carrie's chemistry with Ray and repeatedly attempts to cut off their flirtation, but to no avail. But perhaps the most painful moment for Big is when the trio is squeezed in a cab together on the ride home. Even Big's biggest haters can't help but feel a twinge of sympathy upon watching this uncomfortable situation unfold.
When He Sabatoges His Wedding
Sex and the City: The Movie certainly divides fans, with some considering the 2008 release a gain for the franchise and others vehemently disagreeing. But for fans of the show, it's practically required viewing as it provides a valuable glimpse into Big and Carrie's life together after they reunite in the series finale.
Although they decide to get married - a monumental decision for the man who once told Carrie he'd never wed again - and decide on a modest celebration, things quickly get out of hand after Carrie poses for a lavish photoshoot in a popular magazine. In the end, Big botches the wedding by leaving Carrie at the altar and only changes his mind when it's far too late. Viewers know how much he cares about Carrie, and it's undeniably a devastating situation for the both of them.
When Carrie Spurns His Advances In The Finale
One of Big's saddest moments occurs in the show's second-to-last episode, "An American Girl In Paris (Part Une)," when Carrie seems to be over him for good. Just as she leaves her apartment for a goodbye dinner with the girls, she notices Big parked outside and reluctantly sits in the backseat with him one last time.
He's there to tell her he's made a mistake and is reconsidering their relationship, but after several years wasted chasing after him, Carrie is done. She explodes and tells him to forget he knows her before running off. For many Carrie fans, it's bittersweet yet satisfying to see her finally tell Big off, but for fans of Big, it's a shocking and heartbreaking scene.