Top 10 Celebs Who Suck at Retiring

Going back on your word is never a good look. Welcome to WatchMojo.com, and today we’ll be counting down our picks for the Top 10 People Who Are Bad at Retiring.

For this list, we’ll be looking at actors, musicians, athletes, and authors who, for one reason or another, couldn’t manage to stay retired.

It was a sad day in 2008 when Clint Eastwood claimed that he would no longer be appearing in feature films. A four-time Academy Award winner whose film credits include “The Good, the Bad and the Ugly” and “Unforgiven,” Eastwood felt he’d given his all as an actor and would now focuses solely on directing. He went so far as to give an analogy for why he was hanging em’ up, remarking “You don't want to be like a fighter who stays too long in the ring until you’re not performing at our best." Ironically, he failed to take his own advice and in 2012 appeared in the sports flick, “Trouble with the Curve.”

A two-time Grammy winner and one of the best-selling artists in music history, Garth Brooks had little left to prove when he decided to retire in the fall of 2000. Nevertheless, he’s had a hard time staying retired since then. In 2005, he began performing live again, something his official retirement announcement five years earlier claimed he would no longer do. Then in 2009, he signed a five-year residency at a Las Vegas hotel. His “retirement” officially went out the window in 2014 when he embarked on his World Tour, and released a new album. Clearly the man just loves making music!

When Barbra Streisand announced that she would no longer be playing public concerts, the world let out a collective groan. The Oscar, Tony, Emmy, and Grammy recipient had been a musical mainstay since the 60s, so hearing that she would no longer be belting out tunes to live audiences must have made more than a few diehard fans tear up in disappointment. Thankfully for them, she’s on our list. Streisand went back on her word in 2006 and began touring once again, first with the “Streisand” tour and later with “Barbra Live” and “Barbra: The Music, The Mem'ries, The Magic.”

One can scarcely imagine a world without the twisted yet deeply insightful works of Stephen King. The celebrated author has penned nearly 60 novels to date and we expect that number to only rise what with his seemingly insatiable need to frenetically release new material. However, everything post 1999 almost never happened. It was in the summer of that year that King was struck and almost killed by a car while walking along a highway in his home state of Maine. Due to the pain that it now caused him to sit for long periods of time, the author said he would no longer be writing novels. Since then, he’s released almost 20. Retired? Hardly.

Brett Favre and the word, “retirement,” will forever share a unique bond. The former NFL quarterback first flirted with hangin’ up his cleats in 2002, though nothing came of it. In the ensuing years the Super Bowl winner would constantly be peppered with questions of whether or not he was retiring and he always seemed unsure. Finally, in 2008 he decided he’d had enough and retired from the Green Bay Packers. But it didn’t last long. He soon called the team requesting to be reinstated but they refused… so he signed with the Jets. When they released him in 2009, he claimed to be retired again, but later signed with the Minnesota Vikings. Talk about indecisive!

Arguably the greatest actor of his generation, renowned thespian Daniel Day-Lewis pops up every couple of years to absolutely destroy a role, often walking away with an Academy Award for his work. He first dabbled in retirement after completing “The Boxer” in 1997. He did so in order to pursue his passion for woodworking, later moving to Italy in order to practice shoemaking. You can’t make this stuff up. Thankfully for us, he made his triumphant return in Martin Scorsese’s epic period picture, “Gangs of New York,” in 2002. Since then, he’s continued to churn out jaw-dropping performances, but in 2017 announced that “Phantom Thread” would be his last role. We’ll see about that…

A word to the wise: it’s a little hypocritical to call something a “Farewell Tour” if you don’t actually plan on retiring afterwards. Alas, Cher is not your typical artist. The longtime entertainer whose career has spanned almost six decades announced in 2002 that “Living Proof: The Farewell Tour” would be her last. We will point out that she still planned on making music and appearing in films and TV shows, but she also said that her time touring was over. Of course this all fell apart in 2014 when she went on her “Dressed to Kill Tour.” So much for retirement!

In one of the most highly publicized retirements in sports history, the face of the NBA and everyone’s favorite member of the Toon Squad announced that he’d be leaving the Chicago Bulls in order to pursue a career in baseball. Unfortunately, #23’s skills on the court didn’t translate to the diamond and he returned to the NBA two years later. After winning another three championships in a row, Jordan decided to retire again, this time for good. Just kidding! He’d come back in 2001 to play two seasons with the Washington Wizards! By that point, he’d accumulated so much money playing ball he donated his salary to a relief fund for victims of 9/11.

After completing “The Black Album,” the eighth of his already illustrious career, Jay-Z decided he’d had enough of the rap game and called it quits. In November of 2003, his concert at Madison Square Garden was labeled his “retirement party” with everyone, from Beyoncé to Pharrell, turning up to sing a song or two. Of course he wouldn’t be on this list if he’d stayed in retirement. Mr. Z hooked up with Linkin Park on a collaborative EP a year later, and in 2006 he released his ninth studio album “Kingdom Come.” Since then, he’s continued to churn out music and currently shows no signs of slowing down.





Before we unveil our top pick, here are a few honorable mentions:



Steven Soderbergh





Floyd Mayweather Jr.





Larry King

Osbourne, the heavy metal legend that rose to prominence in the 70s as the lead singer of Black Sabbath, decided to call it quits in 1993. He’d grown tired of a life on the road and decided that his aptly named “No More Tours” tour would be his last. However, in a hilarious turn of events, he’d shun this decision just two years later and embark on “The Retirement Sucks Tour.” How perfect is that? The tour was in support of his newest album, “Ozzmosis.” Two decades later and the embattled rocker is still going strong!