Defiantly defending his DWI arrest, stubborn pop singer Justin Timberlake is alienating fans and business allies alike, and rumors have it that it's about to derail his career.

"This is a case of Justin's Type-A, never-back-down personality getting the best of him and causing real damage. He has some really experienced publicists and managers offering sound advice, but he's not listening to them,” an unnamed source told The National Enquirer.

The best course of action, according to people in the entertainment industry, in situations like Justin's is to own up to the mistake, apologize, and accept responsibility. However, he appears to be attempting to avoid accountability and have the entire case dismissed.

"This kind of behavior really speaks to the dark side of his personality. He's a guy who loves a fight, even when he should know it's a losing battle,” the anonymous insider claimed.

The 43-year-old "Sexy Back" singer was reportedly pulled over in June for allegedly running a stop sign in the upscale Sag Harbor neighborhood of Long Island. Slurred speech, an unsteady gait, bloodshot eyes, and breath with "a strong odor of an alcoholic beverage" were among the symptoms that led the police to suspect Justin of drunkenness.

Justin has pled not guilty to driving while intoxicated and informed the arresting officer that he had only had one drink.

"This arrest has already spoiled some of his career plans, and now his overzealous defense is on the verge of absolutely destroying his reputation. There are a lot of people begging Justin not to go down this road,” the undisclosed insider stated.

Meanwhile, a case that started with Justin's arrest in the Hamptons in June on allegations of drunk driving came to a close on Friday when he pled guilty to driving while impaired.

Justin pled guilty and was ordered to pay a fine of $500 in addition to doing 25 hours of community service for a charity of his choice, The New York Times reported. In addition, he consented to a 90-day suspension of his New York driver's license.

The musician entered the plea at a court hearing in Sag Harbor's 30-seat courthouse; he had initially faced charges related to the more serious offense of driving while intoxicated. A pair of pearls protruded from under his dark T-shirt as he sported a black cardigan and khaki pants.

After the hearing, Justin spoke to media outside the courthouse and asked anyone following the case to take note of his error.

“Many of you have probably been covering me for a lot of my life, and as you may know, I try to hold myself to a very high standard, for myself, and this was not that,” he said.

When a police officer in Sag Harbor stopped a brand-new BMW for erratic driving in the wee hours of June 18, the suspects were taken into custody.

According to an arrest report, Justin was behind the wheel with hazy eyes and an odor of intoxication. According to the report, he had difficulty finishing multiple sobriety tests after getting out of the car. He remained in police detention all night.

The musician informed authorities that he was returning home after imbibing "one martini." During an interview with reporters, his attorney, Edward Burke Jr., maintained that his client was sober at the time of his arrest. At a hearing in August, Village Justice Carl Irace reprimanded Burke for making comments regarding the charges outside of court.

Mr. Timberlake's summer of shame comes to a close with the guilty plea. A deluge of satirical memes and media coverage followed his detention. Sag Harbor's downtown, with its municipal building encircled by apparel boutiques, fancy galleries, and the American Hotel, attracted throngs of reporters and television crews even during his absent court dates. There was surveillance footage from the night of Mr. Timberlake's arrest showing him drinking.

His “Forget Tomorrow” tour has continued unabated despite his legal troubles. He even made light of the claims during a June concert in Boston, and he has continued to play stadium concerts. Astonishingly, Justice Irace allowed Justin to join the August hearing over video conference from an unidentified European location, taking into consideration the demands of the singer's tour schedule.

Justin is scheduled to perform at the Prudential Center in Newark at the end of September as part of a charity show that will benefit a suicide-prevention nonprofit.

Although social media users had a laugh or two at Justin’s expense, some prominent people with ties to the Hamptons sympathized with his public relations headache. In a recent New Yorker profile, the celebrity chef Ina Garten said she felt bad for “poor Justin Timberlake.”

Billy Joel, a resident of Sag Harbor and a man who had three vehicle accidents on Long Island in the early 2000s, told a local news reporter to "judge not, lest ye be judged" when asked about Justin's arrest in June. On Friday, the less well-known inhabitants of Sag Harbor showed no sympathy.

Business Times has reached out to Justin Timberlake for comments.