This 2000s Heartthrob Deemed ‘Most Handsome’ Man Became Hardly Recognizable – What Happened?

In February 2022, he stepped out in Los Angeles in a tight white tank top, flaunting his toned arms, bushy gray beard, and thick, wavy salt-and-pepper hair. This new look was a stark contrast from the clean-cut appearance he maintained during his “Star Trek” fame.

Upon seeing this, some online users stated that he seemed like a homeless man. “Looks like he could fit in with the homeless people on the streets there. I guess times are tough for everyone,” said  one person.

Another suggested, “He’s going for the homeless look. Someone toss him a bar of soap, he likely needs a scrubbing.” Two more users echoed the same sentiments while one wrote, “Looks 55 and homeless! Great character actor!!”

Meanwhile, other people expressed curiosity, with one individual writing, “He was one nice looking guy, I wonder what happened?” Another asked the same question, adding, “It looks like he got stranded in the middle of the jungle for a year.”

“He used to be so hot, now he looks like he’s recovering from something,” someone else reminisced while making comparisons to the star’s current look. Moreover, others remarked that he appeared unrecognizable at first glance. “I’m impressed anyone recognized him. He looks raggedy,” wrote one.

One X user posted a collage of throwback images of the celebrity. “Bad procedure to keep up “Hollywood standards”? Was so handsome. Almost don’t recognize him now. Sad!” said the user. After seeing the star’s raggedy look, another person asked if that was really him, adding, “Didn’t recognize him…”

Although some had been critical of his appearance, others still perceived him to be attractive. One X user called him “One of the most handsome men on Earth.” Someone else said he voted the star as the “Most handsome man in cinema.”

Another admitted she thought the celebrity was a regular guy growing up but that has since changed. “Now, all of the sudden, he’s the most handsome guy I’ve seen,” penned the user. One other person concurred, “He is definitely the most handsome.”

This actor was at the height of his career in the 2000s. He had several guest roles in television shows and made his feature movie debut opposite Anne Hathaway in “The Princess Diaries 2: Royal Engagement” in 2004.

This was followed by other stints in films and TV shows, but the celebrity rose to superstardom after being cast as James T. Kirk in the hit franchise reboot of “Star Trek” in 2009.

From rocking sophisticated, clean, and attractive looks over the years, to looking barely recognizable today, here is the 2000s heartthrob who was deemed “most handsome” before.

Chris Pine in 2004

In 2004, Chris Pine sported a clean-shaven look with short, dark brown hair styled neatly. His youthful face was smooth and free of any facial hair.

At the premiere of “The Princess Diaries 2: Royal Engagement,” Pine maintained a similar clean-shaven look, but with shorter, neatly styled hair. He still channeled a youthful look, with a fresh and vibrant aura.

Pine in 2005

By 2005, Pine’s appearance subtly evolved. His hair remained short but appeared slightly longer and more tousled, adding a hint of casual style.

The Los Angeles native’s face was still clean-shaven, maintaining a clear complexion. His overall look became a bit more relaxed while still maintaining a professional and polished demeanor.

Pine in 2006

In 2006, Pine’s look shifted further as his hair gave him a laid-back yet stylish vibe. The overall appearance blended a relaxed charm with a refined edge, marking his continued evolution in Hollywood.

Pine in 2007

In early 2007, Pine’s style evolved once more. His hair was styled with a bit more volume, giving a fuller look. The star’s overall appearance was sophisticated, with a touch of maturity that added to his charm.

By March 2007, the movie actor’s appearance took on a more mature and slightly rugged edge. His overall demeanor was polished yet relaxed, reflecting his growth in the industry.

Pine in 2010

Three years later, in 2010, Pine’s look showed significant sophistication. As he attended the Academy Awards, his hair was shorter and styled neatly, exuding a more formal appearance. His overall presence was refined and elegant, suited to the prestigious event.

Pine in 2012

Pine presented a sleek and polished appearance in early 2012. He sported a light stubble, giving a rugged touch to his otherwise smooth complexion, and his eyes exuded confidence and charm.

By June of that year, the “Wonder Woman” star’s appearance remained sharp yet slightly more casual. His hair was still well-groomed, giving him a relaxed yet stylish look.

Pine in 2013

Pine blended polished sophistication and a relaxed style in 2013. His hair had a bit of volume and texture, giving it a modern and trendy look. This time, “The Contractor” star sported a light beard.

It was during this period that Pine’s love life made headlines. He was seen locking lips with a beautiful Icelandic beauty queen while in Paris. This reportedly occurred during dinner at an outdoor cafe after the lovebirds visited historic landmarks. They were later seen embracing while taking selfies.

Pine in 2014

In early 2014, Pine showcased a refined and elegant appearance. His hair was styled neatly which complemented his formal look while attending the Golden Globe Awards.

Pine, who appeared in the Western action movie, “Hell or High Water,” had a bit more texture and volume to his tresses and he sported a light beard.

Pine in 2015

Pine exuded classic elegance in early 2015, with his short and sleek hair giving a refined and polished look. The celebrity’s beard accentuated his facial appearance.

Pine in 2016

In early 2016, Pine’s locks on the sides had a bit more length on top, adding volume. The public figure had a light beard, giving a rugged touch to his clear complexion.

In an interview from this period, the star reflected on his fame, saying, “I don’t even feel like I picked it. I just started doing plays in college. And then I went to LA. Then I got an agent. It just sort of rolled like a very slow snowball into what I’m doing now. It’s very weird.”

Pine in 2017

In 2017, Pine opted for a different look when he chopped off his hair as he went bald. The film star revealed that he did it himself using clippers and that it was because he was bored.

“I went through phases. So I had long hair and a beard. And first I did a facial hair thing. That was fun. I did the mustache. I did a little General Sherman. Then I did a full-shaved back (of the head). That was fun for a day,” he explained.

Pine in 2018

Once his hair grew back, Pine showcased a bold appearance with a natural, slightly tousled texture, adding a relaxed yet sophisticated vibe. His overall look was charismatic and commanding, perfectly aligning with the premiere of “Outlaw King.”

Pine in 2019

Pine changed his hairstyle in 2019, opting for a longer hairdo parted in the middle. His overall look was composed and perfectly suited for the Emmy event he attended.

Apart from his looks, Pine revealed that he feels insecure sometimes, “[…]I’m the kid who was made fun of. That insecurity still runs incredibly deep. […] I was walking in this rigid way, and it had a lot to do with having been an insecure kid trying to move protectively. Now, my body is moving in a more healthful way.”

Pine in 2020

In February 2020, Pine attended a Pre-Oscars dinner and sported a refined cut, giving him a sharp appearance. He had a clean-shaven face, emphasizing his smooth and clear skin and his mustache.

At this time, Pine also adopted a more casual and relaxed look. The Hollywood star’s overall appearance was casual yet stylish, suitable for a relaxed outing in Los Angeles with his then-girlfriend, actress Annabelle Wallis.

Pine in 2021

In 2021, Pine showcased a rugged and casual appearance. His hair was longer, styled with a natural wave that added a relaxed yet stylish touch. He sported a full beard, giving a mature dimension to his look.

Amid this period, actress and media personality Audrina Patridge revealed she and Pine briefly dated after meeting in Las Vegas. However, because of their contrasting lifestyles at the time, things fizzled out between them.

Pine in 2022

In March 2022, Pine, who starred in “Just My Luck,” displayed a refined look with longer hair, featuring silver highlights that enhanced his sophisticated appearance.

By July, the 43-year-old adopted a more relaxed and approachable look while attending the Comic-Con. His hair was slightly longer, with a casual wave.

By October, Pine’s hair remained stylishly textured, adding a bit of casual flair. He sported a light stubble, introducing a hint of ruggedness.

At this time, Pine reportedly broke up with Wallis, well-known for starring opposite Tom Cruise in “The Mummy.” The couple had been dating since 2018 after they were first seen together at London’s Heathrow Airport. They confirmed their romance months later.

Pine in 2023

In March 2023, Pine showcased a modern style with his hair in a natural wave, giving a casual look. Meanwhile, his eyes reflected a confident and approachable demeanor.

Later that month, Pine appeared on “Jimmy Kimmel Live!” with a stylish and charismatic look. His hair remained neatly styled, maintaining a sleek appearance.

By November, he attended the “Wish” photo call, sporting a light beard. This introduced a mature and rugged element to the star’s clear complexion.

During this period, there were rumors about the woman he was seen with in Italy. In a Q&A, one person asked whether it was Pine’s girlfriend or employee. In response, one individual claimed that it was not his partner.

Pine in 2024

Pine attended the 49th Chaplin Award Gala on April 29, 2024, in New York City. He looked dapper in a classic black tuxedo, sporting a salt-and-pepper hairdo. The celebrity also had a well-groomed beard, adding to his sophisticated appearance.

That same month, he also attended the premiere of his new movie, “Poolman” and talked about his transformation through the years. Pine said he has reached a point in his life where he does not care anymore.

“This whole film, what I love about what we did is it’s the joy of everything, of design, of clothes, of cinema, of film, of shooting on film, of characters and weird characters,” Pine revealed.

His look for the movie premiere was inspired by his style icon, Lapo Elkann. “The short shorts were definitely inspired by Tom Selleck. There’s no lie about that,” said Pine.

Pine, who currently has longer hair, divulged that he is now experimenting with early 80s Harrison Ford looks. He explained, “So I really like a penny loafer with like a Levi jean and a blazer, I think that’s pretty fly. And Tom Selleck. So I’m in an ‘80s thing.”

Pine, whose publicist made fun of his long hair once, has also been candid about his misfortune when it comes to his appearance. He disclosed in May 2024 that he lost a role due to his “awful skin.”

“I was going out for The O.C., a teenage melodrama. I can understand that they wanted to have pretty people doing pretty things. It’s no fun going out for roles when you have bad skin. It was one of the most traumatic points in my life,” Pine admitted.

Besides losing out on an acting gig due to his skin, Pine has experimented a lot with his appearance over time. He has gone bald and has sported a beard from time to time. However, now it seems he is in a phase of life where looks do not matter as much to him.