He had eight hours behind bars to sober up. On the morning of June 18, Justin Timberlake, who had been arrested at around 1 a.m. for driving while intoxicated in Sag Harbor, N.Y., appeared “shell-shocked,” “bleary-eyed” and “upset,” according to an eyewitness, as the singer was led in handcuffs to his arraignment at the courthouse in the Hamptons village.

The A-lister was accompanied by his lawyer and two other people, adds the eyewitness, but his wife of nearly 12 years, Jessica Biel, who had been filming a TV show in nearby NYC all week, “was not with him.”

That didn’t come as a huge surprise to those close to the couple. “Justin has humiliated her again,” a source says of the actress, who has endured multiple cheating scandals over their 17- year relationship. “This could all lead to a divorce bombshell. No one would be shocked if Jessica issued Justin an ultimatum: Get help — or it’s over.”

Justin Timberlake’s Hard Partying

He denied he was drunk. Though witnesses claimed to have seen him getting “wasted” at the American Hotel bar earlier in the night, Justin claimed he “had one martini” and was following friends home when officers pulled him over for running a stop sign and veering out of his lane. Those same pals reportedly showed up and tried to talk the cops, who didn’t recognize the superstar, out of arresting him.

But Justin, 43, was “glassyeyed,” smelled of alcohol, and “performed poorly” on field sobriety tests, according to the police report. At the station later, he refused a Breathalyzer test, as is his right. (“I look forward to vigorously defending Mr. Timberlake on these allegations,” his lawyer, Edward Burke Jr., said in a June 19 statement after his client was released without bail. Justin is due back in court on July 26.)

This was far from the first time a night of partying ended poorly for Justin. The “Can’t Stop the Feeling!” singer, who admitted in 2002 to getting “plastered” and doing “my fair share of drugs,” has a tendency to “get caught up in his lifestyle, drinking and partying with friends.

Who Is Your Favorite Celebrity Couple?

Jessica is always trying to keep him stable,” says the source. But in April, when Justin embarked on his first tour in five years, “of course he started going out. It worries her because when he’s drunk, he makes bad decisions.”

Justin Timberlake’s Infidelity Rumors

Justin has been accused of being unfaithful. In September 2010, while he and Jessica were together, he reportedly had a weekend fling with actress Olivia Munn in her NYC hotel room after telling her that he and Jessica, 42, had split. (He’s denied it; Olivia’s rep declined to comment on the actress’ personal life.)

Jessica broke up with him in 2011, but they eventually reconciled and they wed in December 2012. But whispers of infidelity continued. “He f–ked around on his wife right before they got married,” one music insider alleged at the time, telling In Touch exclusively that she witnessed Justin “making out on a couch” with another woman in late 2012.

In 2013, a witness claimed to have seen him kissing actress Thaila Ayala in Brazil. A year later, Justin allegedly got flirty at a Paris bar with a backup singer, Zenya Bashford. “He was rubbing and caressing her from behind, dancing in a way that no married man should ever dance with someone who isn’t his wife,” an onlooker said. (He’s denied any wrongdoing.)

In 2019, he was caught in another cheating scandal. “I drank way too much that night, and I regret my behavior,” Justin confessed after being photographed holding hands with his Palmer costar Alisha Wainwright during a boozy night out in New Orleans, acknowledging that he “displayed a strong lapse of judgment.”

Around that time, Justin and Jessica began spending most of their time in Montana. “She wanted to keep him away from temptation,” the source says of the actress, who shares Silas, 9, and Phineas, 4, with the singer. (In a Father’s Day post just two days before his arrest, Justin gushed that the boys had given him his “biggest purpose.”) “They were trying to focus on their family and their marriage. At one point, I’d heard he was offered a big contract for a Vegas residency, and she thought it would be a horrible idea, so he turned it down. She knows how easy it is for him to get caught up in the partying and where that will lead. He doesn’t know how to turn it off.”

But by 2021, he was making headlines again. Justin was rumored to have been spotted “making out with a woman who is not his wife” in Atlanta, where he was filming the movie Reptile. And earlier this year, Playboy model Zoe Gregory alleged that she hooked up with Justin while he was dating Cameron Diaz in the early 2000s.

“He just can’t escape this ‘cheater’ label, and it upset Jessica every time,” says the source. “Her friends fear he’ll break her heart again: Do cheaters ever change?”

So far, she’s stood by her man. “Her friends think she’s married to a loser and hate that so much of her life is taken up with trying to get Justin to stay on the straight and narrow,” says the source. “But the arrest was a wake-up call: It’s time for her to realize she can’t do it alone. If he keeps going down this path, their marriage will be over.”

Have a tip? Send it to us! Email In Touch at contact@intouchweekly.com.