This Hollywood icon’s recent transformation has sparked quite a buzz online, leaving fans doing double-takes at his unrecognizable look. Let’s take a look back at how he appeared in the early days of his career compared to his appearance today.
This ’90s and early 2000s heartthrob, best remembered for his roles in movies like “I Know What You Did Last Summer” and “She’s All That,” once captivated audiences with his youthful charm and good looks. Today, though, fans are reacting with surprise as he looks notably different from his heyday.
The actor at the Hollywood premiere of “The House of Yes,” 1997 | Source: Getty Images
After stepping back from the spotlight to focus on family life, this beloved actor, now in his late 40s, has embraced a more private lifestyle. Here’s a closer look at how this Hollywood veteran’s appearance has evolved over the years.
1996
Known for his youthful charm, the celebrity, whose father was a famed actor and comedian, was seen in 1996 with a fresh face, short dark hair, and a sleek tuxedo look, attending the Golden Globe Awards.
The actor at the 53rd Annual Golden Globe Awards on January 21, 1996, in Beverly Hills, California. | Source: Getty Images
1998
By the late ’90s, he captured hearts and dominated red carpets with effortless style. In 1998, the actor attended a movie premiere sporting a suit paired with a blue shirt while rocking a spiky hairstyle.
The actor at the Westwood premiere of “I Still Know What You Did Last Summer,” 1998 | Source: Getty Images
By December, the public figure opted for a relaxed navy blue outfit at the “Shakespeare in Love” premiere, further embodying his effortless charm.
Kimberly McCullough and the actor at the Beverly Hills premiere of “Shakespeare in Love,” 1998 | Source: Getty Images
During this period, the film star was romantically involved with Kimberly McCullough, who was his date at the premiere. Years later, she reflected on their relationship with humor, writing on X, “This is when you say ‘Thank you universe for not letting me marry this one!’ What a douche.” The actress was reacting to an article about her former lover, who talked negatively about a fellow celebrity.
1999
As the decade came to a close, the actor’s appearances reflected the peak of his early fame. In January 1999, he posed with an introspective look, dressed simply in a light sweater.
The actor at the Trump International Hotel and Towers on January 14, 1999 | Source: Getty Images
By August, the Hollywood star appeared in the film, “Head Over Heels.” One scene showed him in a crisp blue shirt, presenting a clean-cut style.
The actor on the set of “Head Over Heels,” 1999 | Source: Getty Images
In September, he walked the red carpet with Kimberly, sporting a dark suit with a burgundy shirt, giving him a refined and classic look.
The actor and Kimberly McCullough at the Teen Choice Awards on September 10, 1999, in Los Angeles. | Source: Getty Images
Later in November, he kept things understated at the “End of Days” premiere, choosing a soft gray sweater that matched his easygoing yet confident aura.
The actor at the Hollywood premiere of “End of Days,” 1999 | Source: Getty Images
2000
With the turn of the millennium, the actor’s look evolved along with his career. In June 2000, he appeared in a scene from “Boys and Girls” with a thoughtful expression, resting his chin on his hand, exuding a contemplative vibe.
The actor on the set of “Boys And Girls,” 2000 | Source: Getty Images
By August, he attended an award ceremony, radiating a fresh-faced look in a simple gray T-shirt, capturing the easygoing essence that endeared him to fans.
The actor at the Teen Choice Awards on August 6, 2000, in Santa Monica, California. | Source: Getty Images
2001
By 2001, the celebrity surprised fans with a fresh transformation, embracing an edgier aesthetic that marked his growth. In January, he attended the Golden Globe Awards, sporting a bold platinum-blond look paired with a sharp black suit and silver tie.
The actor at the 58th Annual Golden Globe Awards on January 21, 2001, in Beverly Hills, California. | Source: Getty Images
Later, in August, he attended a movie premiere with a closely shaved head and casual attire, showcasing his laid-back approach amidst his ongoing popularity.
2004
As 2004 unfolded, Freddie balanced the excitement of movie premieres with the demands of on-set roles. He channeled a laid-back style when he showed up to the “Scooby-Doo 2” premiere in a graphic tee and cap.
Freddie Prinze Jr. at the world premiere of “Scooby-Doo 2: Monsters Unleashed,” 2004 | Source: Getty Images
By October, the Los Angeles native took on a tougher look while filming a scene in New York for the movie “Nailed Right In.”
Freddie Prinze Jr. on the set of “Nailed Right In,” 2004 | Source: Getty Images
Later that year, Freddie honored his late father, Freddie Prinze, with an emotional star-unveiling ceremony in Hollywood. He expressed deep gratitude for the love and respect shown to his father’s memory.
Freddie Prinze Jr. tearing up as he speaks during a star dedication ceremony for Freddie Prinze on the Hollywood Walk of Fame on December 14, 2004, in Hollywood, California. | Source: Getty Images
Freddie hoped his father’s Hollywood star would bring joy to all who passed it, celebrating the legacy of laughter and love his late dad had left behind.
Freddie Prinze Jr. at the Hollywood Walk of Fame ceremony in honor of his late father, Freddie Prinze, on December 14, 2004, in Hollywood, California. | Source: Getty Images
2006
By 2006, the public figure continued to charm audiences with his approachable style. In February, he appeared on MTV’s “Total Request Live” wearing a casual brown jacket over a red shirt, as he engaged with fans on stage.
2020
Stepping into 2020, Freddie embraced a relaxed, down-to-earth style on screen. His hair, now a refined gray, paired with a casual black jacket and light shirt, added a grounded warmth to his appearance.
Freddie Prinze Jr. on the set of “Punky Brewster,” 2020 | Source: Getty Images
2023
Freddie’s look in 2023 showcased his evolving yet effortlessly charismatic facial features. In January, he sported a neatly groomed beard that framed his face, adding definition to his jawline, with a relaxed expression under his signature fedora.
Sarah Michelle Gellar and Freddie Prinze Jr. at the Los Angeles premiere of “Wolf Pack,” 2023 | Source: Getty Images
By October, his gray hair and demeanor accentuated a more distinguished look, showing a balance of maturity and warmth.
In December, the actor’s soft grin and expressive eyes radiated holiday cheer, complemented by a subtle blend of gray in his beard, emphasizing his grounded and timeless charm.
2024
Freddie’s family life remains at the heart of his journey, adding depth to his enduring appeal. In September 2024, he celebrated 22 years of marriage with Sarah, sharing the milestone on Instagram. The couple has two children, daughter Charlotte Grace, born in 2009, and son Rocky James, welcomed in 2012.
