Celebs Who Are Bad at Retiring
Some stars walk away with a grand farewell, then feel the pull to come back. Careers span decades, plans change, and the stage or the field keeps calling. The result is a long list of artists and athletes who have said goodbye more than once, only to return for another run.
This roundup looks at famous retirements that did not stick, with quick timelines of what was announced and what happened next. From championship comebacks to reunion tours to surprise returns to the director’s chair, these are the careers that prove retirement can be more of a pause than a full stop.
Michael Jordan
Jordan first retired from the NBA in 1993, stepped into minor league baseball, then returned to the Chicago Bulls in 1995 and won three more titles before retiring again in 1999. He came back in 2001 with the Washington Wizards and played two seasons before retiring for a third time in 2003.
He later moved into ownership and executive roles with the Charlotte franchise while remaining one of the sport’s most visible figures through endorsements and philanthropic work. His on court returns stand as the gold standard for high profile unretirements in team sports.
Tom Brady
Brady announced his retirement in February 2022, then reversed course a few weeks later and played the 2022 season for Tampa Bay. He retired again in February 2023 and shifted to media and business ventures.
His post playing path included a broadcast role and investments across sports and entertainment. The single season comeback after the first announcement kept his career totals climbing before he finally stepped away.
Brett Favre
Favre announced his retirement in 2008 after a long run with Green Bay, then joined the New York Jets for the 2008 season. He said he was done again in early 2009, only to sign with Minnesota later that year.
He led the Vikings to a deep playoff run in the 2009 season and played again in 2010 before finishing his career. Multiple announcements and changes of heart made his exit one of the most winding in modern football.
Rob Gronkowski
Gronkowski retired in 2019 after winning another championship with New England. He returned in 2020, reunited with Tom Brady in Tampa Bay, and won the title again that season.
He announced a second retirement in 2022 after two productive years in Tampa Bay. Off the field he continued with endorsements and media appearances while keeping the door cracked in interviews more than once.
Conor McGregor
McGregor declared retirement in 2016, then headlined major events later that year and returned again after further retirements in 2019 and 2020. He booked high profile fights in 2020 and 2021, including a win over Donald Cerrone and bouts with Dustin Poirier.
Following injury in 2021 he alternated between teasing comebacks and training clips. His pattern of announcements followed by returns made him one of the most notable figures in combat sports for on again participation.
Floyd Mayweather Jr.
Mayweather announced retirement in 2007 after a dominant run, then returned in 2009 and continued to win marquee fights. He retired again in 2015 with a perfect professional record and came back in 2017 for a heavily watched bout with Conor McGregor.
He moved into exhibitions around the world after that milestone win. The mix of official retirements and selective returns kept his name active years beyond his full time championship run.
Michael Phelps
Phelps retired after the 2012 Olympics, then resumed training in 2014 and made the United States team for the 2016 Games. He won multiple medals in Rio and closed out that meet as one of the most decorated Olympians in history.
He stepped away again after 2016 and focused on family, business partnerships, and advocacy work in mental health and water safety. The mid cycle return added a final chapter of dominance to an already unmatched medal haul.
The Eagles
The band launched Farewell 1 Tour in 2004 and kept performing long after, including releasing a studio album in 2007. Lineup changes followed the passing of Glenn Frey, with Deacon Frey and Vince Gill joining for later tours.
They announced The Long Goodbye tour in 2023 and continued scheduling shows beyond the first wave of dates. The name of the early farewell became a running joke for fans as the group extended its live legacy.
Kiss
Kiss staged a Farewell Tour in 2000, then returned to the road and continued for many more years with lineup shifts. They started the End of the Road World Tour in 2019 and brought it to a close in 2023 with a final show in New York.
Immediately after, the group unveiled a new era built around digital avatars and future performances in that format. The approach allowed the brand to keep performing in a new way even as the touring lineup stepped off the stage.
Mötley Crüe
The band signed a public agreement in 2014 that was intended to stop future touring after a final run. In 2019 they announced that the agreement was terminated and confirmed plans for a large scale return.
They launched a stadium tour in 2022 with Def Leppard and kept going with international dates in 2023. A lineup change put John 5 on guitar as they added new music and more shows to the post retirement era.
LCD Soundsystem
LCD Soundsystem played a widely publicized final show at Madison Square Garden in 2011 and paused the project. The band returned in 2015, headlined major festivals in 2016, and released a number one album in 2017.
They followed with multi night residencies in New York and London and continued to perform select runs. The initial sendoff became part of the lore, while the reunion restored the group as a regular presence on live calendars.
Jay-Z
Jay-Z framed 2003 as the end of his recording career with a series of farewell moments that year. He returned in 2006 with a new album and resumed touring and collaborations soon after.
Subsequent releases and joint projects kept him at the top of festival and arena bills. The retirement storyline became a brief chapter in a longer run that extended across music and business.
Garth Brooks
Brooks announced his retirement in 2001 to focus on family life. He returned with a Las Vegas residency in 2009 and then relaunched full scale touring in the middle of the next decade.
He added a stadium tour starting in 2019 and later launched a new residency in Las Vegas. Alongside touring he opened a bar and live venue in Nashville and kept releasing new music.
Cher
Cher embarked on a farewell tour from 2002 to 2005 and then resumed live performances with a Las Vegas residency in 2008. She refreshed her set lists over multiple runs and added new material along the way.
She toured arenas again in 2014 and returned to the road for another global run starting in 2018. Even after pause periods she continued to schedule select concerts and television appearances.
Barbra Streisand
Streisand performed a famous open air concert in 1967 and then avoided touring for decades. She returned in 1994 with a sold out run that yielded one of the highest grossing tours of its era.
She followed with limited engagements in the 2000s and added carefully chosen shows in the 2010s. The pattern balanced long breaks with major events that still drew massive demand.
Frank Sinatra
Sinatra announced retirement in 1971 after a long recording and touring career. He returned in 1973 with a new album and a television special and resumed performances.
He continued to record and tour for years after the comeback. His later concerts drew multi generational audiences and kept classic arrangements in rotation well into the 1990s.
The Who
The Who billed their 1982 run as a farewell and then regrouped for major events later in the decade. They returned to large scale touring in 1989 and kept performing in the following decades.
They released new studio music in the 2000s and 2010s and added orchestral tours to the mix. The early promise of goodbye turned into a model of periodic reinvention on stage.
Steven Soderbergh
Soderbergh said he was stepping away from feature filmmaking in 2013 after releasing ‘Side Effects’ and the television film ‘Behind the Candelabra’. He explored television with the series ‘The Knick’ and experimented with new formats.
He returned to features with ‘Logan Lucky’ in 2017 and followed with projects including ‘Unsane’, ‘High Flying Bird’, ‘The Laundromat’, ‘Let Them All Talk’, ‘No Sudden Move’, and ‘Kimi’. He also created the series ‘Full Circle’ and premiered new work on the festival circuit.
Hayao Miyazaki
Miyazaki announced retirement after ‘Princess Mononoke’ in the late 1990s, then returned to direct ‘Spirited Away’. He later announced retirement again after ‘The Wind Rises’ and shifted to a leadership role at Studio Ghibli.
He resumed directing and completed ‘The Boy and the Heron’ in 2023. After its success he signaled continued development work at the studio as new ideas took shape.
Jon Stewart
Stewart left ‘The Daily Show’ in 2015 following a long run as host and focused on film and advocacy projects. He returned to television with ‘The Problem with Jon Stewart’ and continued producing and writing.
He came back to ‘The Daily Show’ in 2024 to host episodes during the election cycle while remaining an executive producer. The return brought him back to the desk years after his original farewell.
Share your favorite unforgettable unretirement in the comments and tell us who else should be on this list.