Ever since Hollywood has been creating movies and stars, they have wanted to find ways to extend these stars’ reach to get the most attention and influence. Before social media and streaming, most people got their entertainment from the few highest watched channels and popular celebrity gossip magazines like People or Teen Vogue. So it’s understandable that award ceremonies for celebrity work have become much more than a dinner and trophy for actors. Created in 1929, the Academy Awards were the first to honor the year’s best actors, producers, directors, writers, and countless other production jobs that audiences may not appreciate. Award shows aren’t just about honoring talent—they’re massive promotional machines that shape careers, boost sales, and influence industry trends. Scandals, feuds, and romances are heavily covered, making people more invested in who showed up with whom and what drama might unfold. Entire TV shows and specials like E! Live on the Red Carpet were created throughout award seasons to ensure consumers could stay up to date on the news.
Awards shows were even able to bring about cultural and technological changes in society. The work of fashion designers had been gaining recognition since the 50’s, but award shows helped get their names out even further. Designers could soon find more widespread fame from a celebrity wearing their dress on the red carpet than during fashion week. Best & worst dressed lists became a staple in entertainment media, fueling an entire industry around critiquing fashion like E! Fashion Police. The award show tech changes were also important to how they have evolved. During the early stages, all award recipients were chosen by a panel of industry elites, however, smartphones and social media inspired the idea for text in voting. This gave fans the ability to vote for their favorite star in real time throughout the event. With this in mind, shows like the American Music Awards and the Billboard Music Awards were created to give out entirely fan-voted trophies.
Oscar Parties
Live award shows like the Oscars and Grammys were so anticipated that they even created a new type of party during the 90’s and into the early 2000’s. Hosts would throw an Oscars party during the airing of the award show and invite friends. Many people embraced old Hollywood glamour, decorating with gold and black, diy red carpets, and movie-related props like clapboards and film reels. Some hosts encouraged guests to dress up in formalwear, mimicking the celebrities at the actual event, while others kept it cozy with pajama parties. Hosts would even print Oscar ballots for their guests to predict winners for each category. Guests could often enjoy movie themed snacks as well such as buttered popcorn, m&m’s, and soda in themed cups. Some viewing parties would be held at bars or lounges and include commentary and events like “best dressed” contests for attendees.
Best dressed
Female:
Jennifer Lopez has had countless iconic award show moments, solidifying her status as a fashion and pop culture icon. Her 2000 Grammy Awards dress is one of the most iconic red carpet moments in history. Designed by Versace, the sheer, plunging jungle-print gown featured a deep V-neckline that extended almost to her stomach, with flowing, tropical-patterned fabric that draped to the floor. While we don’t think much of a celebrity showing skin on the red carpet these days, J.Lo’s dress was the definition of a trend setter. It truly pushed the boundaries of what could be considered formal wear for an event like the Grammys. The moment she stepped onto the Grammys stage, the dress became an instant sensation, dominating headlines and cementing J.Lo as a style icon. Stars at award shows after this moment would only continue to try and have the best dress and garner the most reaction. What truly made the dress legendary, however, was its influence on internet history—so many people searched for photos of J.Lo that night that it inspired Google engineers to create Google Images. This dress has it’s own Wikipedia page, just the dress.
Halle Berry arrived at the 2002 Oscars as just the 7th black woman to be nominated for Best Actress since 1950. She was a front-runner to win her historic award and chose to walk the carpet in a burgundy Ellie Saab sheer bodice gown with floral appliques. The dress also featured a drop waist with a gathered satin skirt and train. The combination of delicate embroidery and bold transparency made it one of the most daring yet sophisticated looks ever seen at the Oscars. history was the moment it was worn—Halle Berry became the first Black woman to win Best Actress, giving an emotional acceptance speech while draped in this beautiful gown. The dress became a symbol of representation, triumph, and breaking barriers in Hollywood, ensuring its place as not just a fashion moment, but a cultural milestone. Even decades later, the gown remains one of the most celebrated and referenced red carpet looks of all time.
Charlize Theron was nominated for Best Actress at the Oscars in 2004 for her work in Monster (2003). Her gown was a sleek, silky white gold dress with a body-hugging silhouette, featuring a delicate train that flowed effortlessly as she walked. What truly made the look stand out was Charlize’s radiant styling—her golden tan, side-swept retro curls, and glowing confidence made her look like a classic Hollywood movie star reborn. Her gleaming appearance marked a transformation to her unglamorous and grungy styling in Monster, giving her outfit all the more hype.
Male: While it took men a little longer to embrace fashion changes, by the early 2000’s, some actors enjoyed picking out a colorful or unique suit to display. These men helped paved the way for those who came after to express themselves through fashion.
Prince was well known for arriving to the Grammys or Oscars with a brightly colored suit and matching accessories. One of his best remembered award show looks was a purple jacket and white pants worn at the 2005 Oscars. For the 2005 People’s Choice Awards, Prince wore a flowing white suit with flared pants, matching white heeled boots, and a flowing hood that gave the outfit an ethereal quality. He understood how to tell a story through his clothing.
Fans could also always count on Justin Timberlake to pull out a trendy outfit for fancy occasions. His outfit for the 2000 MTV movie awards included an oversized black leather coat with ruffle accents and a bedazzled headband, and no one could forget his infamous 2001 double denim look with Britney Spears at the 2001 VMAs. His love for oversized suits was a signature, typically worn without a tie, giving him a relaxed but polished red carpet presence. A prime example was the 2002 Grammys, where he rocked a baggy gray suit with an open dress shirt and a chain. Regardless of the phase, Timberlake consistently influenced men’s fashion, mixing hip-hop-inspired streetwear with classic popstar polish. He even helped push the sneakers-with-suits trend, frequently pairing Nike Dunks or Adidas Superstars with formalwear.
Will Smith’s 2000s style was the perfect blend of classic Hollywood elegance and modern, relaxed tailoring. He was known for his sleek, well-fitted suits, often opting for monochromatic color palettes in shades of black, navy, or gray. Unlike many of his peers who embraced oversized trends, Will kept his suits perfectly tailored, striking a balance between sophisticated and effortless. At more formal occasions like the 2002 Oscars, he kept it classy with well-fitting black suits, outside of formal events, Will’s casual red carpet fashion showcased his cool, confident style. He often rocked leather jackets, fitted jeans, and designer sneakers, and his favorite black sunglasses. Will also embraced monochrome suits, such as his standout white-on-white ensemble at the 2004 MTV Movie Awards.
Most memorable stunts and Controversies
In 1999, South Park creators Matt Stone and Trey Parker decided to try adapting their once paper story into a full length movie. The movie quickly became a beloved part of the franchise and even earned an Academy Award for best original song for “Blame Canada”- a humorous ballad about blaming Canadians for American children’s bad behavior. But in their usual fashion, the pair didn’t want to put on suits and show up in a limo, take red carpet pictures or make small talk with reporters. So they celebrated in a very fitting way, by commissioning recreations of J.Lo’s iconic 2001 green Versace dress and Gwyneth Paltrow’s 1999 baby pink satin Ralph Lauren gown. They wore these dresses, heels, matching purses, and wigs throughout the entire event. That wasn’t all, however, because they later revealed they had taken tablets of LSD before they walked the carpet as well and were clearly out of it. Their prank was a perfect mix of satire, absurdity, and anti-Hollywood humor, mocking the over-the-top glamour of the Oscars while staying completely in character. The stunt remains one of the most legendary red carpet moments in Oscars history. To add humor to confusion, the pair answered any and all outfit questions with the whimsical phrase, “It’s a magical night tonight”.
One of the most shocking and talked-about red carpet and stage moments of the 2000s happened at the 2003 MTV Video Music Awards, when Madonna kissed both Britney Spears and Christina Aguilera during a live performance. The moment came during their iconic opening number, which was a recreation of Madonna’s 1984 Like a Virgin performance, with Britney and Christina dressed as brides and Madonna as the groom in a black tuxedo and top hat. During the performance, Madonna leaned in and kissed Britney first, drawing a massive reaction from the crowd. However, as she then turned and kissed Christina, MTV’s cameras cut away to show Justin Timberlake’s reaction, missing the second kiss in real-time. The moment was controversial, provocative, and a major publicity stunt, generating headlines worldwide and solidifying Britney’s and Christina’s roles as pop princesses following in Madonna’s footsteps. It also played into Madonna’s long standing reputation for pushing boundaries, as she was known for her shock-factor performances. The kiss remains one of the most memorable pop culture moments of the 2000s.
In a move that solidly separated 2000’s looks from those that would come in the 2010’s, Lady Gaga decided to start the decade with a statement. Not widely known outside of a few hit singles at this point, Gaga proved that she would always be herself and arrived at the show in a dress made entirely of raw meat, designed by Franc Fernandez. The garment reportedly weighed over 50 pounds and included matching boots, a purse, and a headpiece- all made of meat. The stunt was quickly and widely criticized, especially from animal rights groups, with many unable to look past the jarring nature to see any deeper meaning, however, she didn’t wear it for simple shock value. Lady Gaga told reporters that the purpose of her dress was to encourage others to stand up for what they believe in and show her disagreement with the U.S. Military “Don’t Ask, Don’t Tell” policy. We haven’t even mentioned the record 13 award nominations Gaga was up for that year and she would win 8 of them- including accepting the award for Video of the Year while wearing a meat dress, next to Cher.
