Celebrity Scandals From The 2000s You Forgot About

In 2003, the American television personality and businesswoman was indicted on charges of conspiracy, obstruction of justice, and securities fraud due to her involvement in a December 2001 insider trading scheme surrounding the biopharmaceutical company ImClone Systems. After being tipped off by her broker, Stewart sold about 4,000 shares in the company just a day before the FDA announced an experimental antibody ImClone developed had failed to obtain approval. The wildly successful entrepreneur was found guilty of conspiracy, obstruction of justice, and of lying to investigators after her 2004 trial; resulting in a sentence of 5 months in prison, followed by 5 months of house arrest, and 2 years probation as well as a fine of $30,000. Stewart reported to a minimum security West Virginia prison in October 2004 and was, according to her, given the nickname “M. Diddy”.

In November 2002, Jackson held his then 9 month-old son, Prince Michael II (then chiefly known by his nickname “Blanket”), over the ledge of his Berlin hotel room’s balcony as he greeted a mass of fans who’d congregated below. By the early 2000s, Jackson had already faced allegations of child molestation and began engaging in increasingly erratic behavior, essentially squandering the modicum of public goodwill he’d had remaining and inviting a deluge of scathing tabloid coverage. In a twist of mordant irony, Jackson was actually in Berlin to accept an award for his charity work benefitting children.

Brad Pitt and Jennifer Aniston’s 2005 divorce marked not only the destruction of one of Hollywood's most beloved couples, but also the inception of one of its most notorious. When Pitt and Aniston announced their separation after 5 years of marriage, a flurry of rumors began swirling around the couple, predominantly focusing on Pitt’s alleged extramarital affair with his Mr. & Mrs. Smith costar Angelina Jolie. Jolie and Pitt began their public relationship shortly after Pitt announced his divorce from Aniston and were subsequently given the pithy couple’s portmanteau “Brangelina”, invoking the ascension of a new celebrity power couple for the public to aspire to and hyperfixate upon. The sudden dissolution of Aniston and Pitt’s marriage was reflective of the deterioration of the veneer of marital bliss that’d become inextricably tied to wealth, beauty, and celebrity.

Amidst an acrimonious child custody battle with ex-husband Kevin Federline, Spears entered a Tarzana, California hair salon in February 2007 requesting to have her head shaved. After the stylist initially refused Spears’ request, the singer grabbed a nearby electric razor and began shaving her head herself while a horde of paparazzi circled the salon like buzzards, snapping photos of the singer inside. Though Spears has yet to discuss the incident in great detail, media speculation for the star’s sudden decision ranged from evidence of a complete psychotic break, to an effort to avoid follicle drug testing and risk hurting her case for sole custody of her and Federline’s 2 children. The salon incident ignited further tabloid scrutiny to Spears’ private life and would later be weaponized by her father, Jamie Spears, to place her under a suffocating conservatorship the American singer would subsequently remain under until late 2021.

Despite the legendary late night host already having a storied history of humiliating and demeaning women on his show (badgering Janet Jackson about her Superbowl fiasco, putting a strand of Jennifer Aniston’s hair in his mouth mid-interview despite her protestations, performing a bit speculating the first words of Monica Lewinsky’s forthcoming biography with 10 unimaginative, stomach turning one-liners), it wasn’t until 2009 Letterman was made to publicly apologize for some of his behavior. Letterman expressed regret for engaging in inappropriate sexual relationships with female staff members after a CBS News producer, Robert Halderman, attempted to extort the late night host with information about his extramarital affairs. Notably, Letterman apologized for the compromising positions he’d put women on his staff in and then directly to his wife, Regina Lasko, a former production manager on his show.

Gibson was arrested for driving under the influence of alcohol in the early hours of July 28, 2006 after being spotted driving erratically on the Pacific Coast Highway in Malibu, California. During the arrest, Gibson made a slew of vitriolic, antisemitic comments to the arresting officer including “Jews are responsible for all the wars in the world”. The audio recording of the arrest was subsequently leaked to the press, leading to widespread criticism and condemnation of the Braveheart director. Gibson later pleaded no contest to the DUI charge and was sentenced to 3 years of probation, mandated participation in an alcohol education program, and ordered to pay fines and restitution for his offense. The actor-director later apologized for his behavior, sought treatment for alcoholism, and met with leaders of the Jewish community in an attempt to make amends for his actions.

In 2008, the now-defunct Gawker blog posted a leaked video Cruise had recorded in 2004 for the Church of Scientology as a part of their recruitment (i.e. indoctrination) efforts. The 9 and a half minute video shows Cruise openly espousing Scientology’s controversial dogma with a deeply unsettling zeal despite Scientology’s extensive history of coercion, abuse, and exploitation of its members. Since joining Scientology in the 1980s, Cruise has become Scientology’s most prolific member, coming to serve as the Church’s defacto public face and straw man, subsequently garnering Scientology an inordinate amount of legitimacy and credence in the public consciousness despite its exhaustive, widely available record of reprehensible behavior.

During the Super Bowl XXXVIII halftime show, surprise performer Justin Timberlake ripped off a piece of Jackson’s costume during a performance of “Rock Your Body”, revealing Jackson’s bare breast covered by a nipple shield for less than a second, thereafter coining the term “wardrobe malfunction” in the public lexicon. Despite their equal participation in the debacle, Timberlake emerged from the scandal widely unscathed while Jackson’s career suffered immensely, leading to her music becoming subject to innumerable blacklists as well as her disinvitation from that year’s Grammy Awards. Jackson’s media vilification later opened public dialogue surrounding arbitrary media censorship, brazen gender inequality, and the inherent sexualization of female bodies.

Amid a quarrelsome custody battle with ex-wife Kim Basinger in 2007, Baldwin left his daughter Ireland, then just 11 years old, a truly vile voicemail referring to her as a “thoughtless little pig” after she’d missed a scheduled phone call with him. Ireland, now 27, has seemingly forgiven her father, even making light of the voicemail during her father’s Comedy Central Roast in 2019. Basinger’s team was later accused of leaking the voicemail to the press, an assertion they’d vehemently deny.

The Australian actor was arrested at New York City’s Mercer Hotel after he’d thrown a phone at a hotel employee when he’d become frustrated by a malfunctioning line. The phone struck the employee in the face resulting in a laceration they'd sought treatment for at a nearby hospital following the altercation. Crowe later pleaded guilty to third-degree assault and issued a public apology expressing regret for the incident.