Staying relevant for more than two decades isn’t a given in show business. Still, many singers and actors have managed to captivate their audiences for years, sometimes undergoing a makeover or reinventing themselves to grow their careers.
Some were thrust into the spotlight as teenagers and only learned to navigate fame as adults. Others, by contrast, were always comfortable with their celebrity status but later decided to prioritize their privacy after spending much of their lives on TV sets.
Each snapshot of the following A-listers represents a different stage of their careers, reminding us how far they’ve come and why they possess that special quality that makes their success endure.
Below, Bored Panda has compiled now-and-then photos of 25 stars, taken in 2005, 2015, and 2025, to honor their talent and wrap up the year with a nostalgic trip down memory lane.
Discover more in 25 Then And Now Shots Of Stars In 2005, 2015 And 2025, Including One Who Was Left "Disfigured"
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#21 Britney Spears
Britney starred in Mickey Mouse Club at age 11 alongside other up-and-coming artists like Justin Timberlake and Christina Aguilera.
After the children’s variety show, she signed a contract with Jive Records and, in 1999, released her first single, …Baby One More Time, which reached the top of the Billboard Hot 100 chart.
She followed up with hits like Oops!... I Did It Again, I’m a Slave 4 U, and Toxic. A few years later, in 2011, Britney rebounded with the successful Femme Fatale.
Throughout her career, she struggled with mental health issues and was placed under a strict conservatorship between 2008 and 2021.
The Princess of Pop has described the conservatorship—which gave her father control over her estate, career, and other aspects of her personal life—as “a*****e.”
After the children’s variety show, she signed a contract with Jive Records and, in 1999, released her first single, …Baby One More Time, which reached the top of the Billboard Hot 100 chart.
She followed up with hits like Oops!... I Did It Again, I’m a Slave 4 U, and Toxic. A few years later, in 2011, Britney rebounded with the successful Femme Fatale.
Throughout her career, she struggled with mental health issues and was placed under a strict conservatorship between 2008 and 2021.
The Princess of Pop has described the conservatorship—which gave her father control over her estate, career, and other aspects of her personal life—as “a*****e.”
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#22 Taylor Swift
Taylor began learning guitar at age 12 and signed her first music contract with Sony/ATV Tree Publishing at 14.
In 2005, she released her self-titled debut album, whose first single, Tim McGraw, peaked at number five on the US Billboard 200 chart.
The teenage country musician followed up with another successful album, Fearless, in 2008. The record featured hits like Love Story and You Belong With Me.
Over time, she began leaning more strongly into pop sounds, working with producers Max Martin and Shellback on her 2012 album Red.
Fast-forward to 2025: at 35, Taylor is one of the best-selling music artists of all time, having won 14 Grammy Awards, released 12 albums, and sold out stadiums around the world.
In 2005, she released her self-titled debut album, whose first single, Tim McGraw, peaked at number five on the US Billboard 200 chart.
The teenage country musician followed up with another successful album, Fearless, in 2008. The record featured hits like Love Story and You Belong With Me.
Over time, she began leaning more strongly into pop sounds, working with producers Max Martin and Shellback on her 2012 album Red.
Fast-forward to 2025: at 35, Taylor is one of the best-selling music artists of all time, having won 14 Grammy Awards, released 12 albums, and sold out stadiums around the world.
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#23 Amanda Bynes
Amanda began her career as a child actor on the 1996 Nickelodeon series All That and later starred in her own spin-off, The Amanda Show.
She went on to appear in She's the Man, Hairspray, and her final film, the 2010 comedy Easy A.
Amanda quit acting after struggling with mental health and substance dependency issues. She spent nearly nine years under her parents’ conservatorship, which concluded in 2022.
After stepping away from Hollywood, she graduated from the Fashion Institute of Design & Merchandising (FIDM) and launched a fashion capsule with designer Austin Babbitt.
She went on to appear in She's the Man, Hairspray, and her final film, the 2010 comedy Easy A.
Amanda quit acting after struggling with mental health and substance dependency issues. She spent nearly nine years under her parents’ conservatorship, which concluded in 2022.
After stepping away from Hollywood, she graduated from the Fashion Institute of Design & Merchandising (FIDM) and launched a fashion capsule with designer Austin Babbitt.
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#24 Cristiano Ronaldo
The Portuguese footballer has received five Ballon d'Ors and won five Champions Leagues throughout his career, holding the record for most goals in the European competition.
The 40-year-old began his career playing for Sporting CP in Portugal before signing with Manchester United in 2003.
In 2009, he joined Real Madrid in a deal worth €94 million, which was then the most expensive football transfer in history.
He later moved to the Serie A, signing for Juventus in 2018. In 2021, he returned to Manchester United before joining Al-Nassr, his current club, two years later.
The 40-year-old began his career playing for Sporting CP in Portugal before signing with Manchester United in 2003.
In 2009, he joined Real Madrid in a deal worth €94 million, which was then the most expensive football transfer in history.
He later moved to the Serie A, signing for Juventus in 2018. In 2021, he returned to Manchester United before joining Al-Nassr, his current club, two years later.
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#25 Mickey Rourke
Mickey broke through in the 1980s with supporting roles in films like Body Heat and Diner. Soon after, he rose to leading-man status in films such as Rumble Fish, The Pope of Greenwich Village, and 9½ Weeks.
The Golden Globe winner, who had a reputation for being difficult to work with, drifted away from Hollywood and began a career as a pro boxer in 1991.
He made an acting comeback in the 2000s, with roles in films like Once Upon a Time in Mexico, Sin City, and The Wrestler.
Earlier this year, the Iron Man 2 actor was evicted from the Celebrity Big Brother house in the UK for making homophobic remarks toward fellow housemate JoJo Siwa.
The Golden Globe winner, who had a reputation for being difficult to work with, drifted away from Hollywood and began a career as a pro boxer in 1991.
He made an acting comeback in the 2000s, with roles in films like Once Upon a Time in Mexico, Sin City, and The Wrestler.
Earlier this year, the Iron Man 2 actor was evicted from the Celebrity Big Brother house in the UK for making homophobic remarks toward fellow housemate JoJo Siwa.
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