8 Celebs Who Made A Comeback And Failed (And 8 Who Were Actually Successful)

Don’t call it a comeback: they’ve been here for years! Thanks to the changeable nature that is Hollywood – with all its temptations, vices, and pitfalls – many celebs might find it impossible to replicate the success they once enjoyed once they’ve moved onto a new project or gotten older. Personal issues can also have a major role in a star’s downward spiral, from which many never recover. Illegal substances are plentiful in Hollywood, and celebs have the means to acquire them, so falling into partying is an easy way to lose out on work, fame – and all hope of a comeback.

On the upside, we also have those who managed to turn things around. Even when they were at rock bottom, unemployable and with a bad reputation, these celebs managed to pull themselves up, dust themselves off, and get back to work, for which they were richly rewarded. It seems that the Hollywood comeback story can go one of two ways: success or failure. While everyone wants to be the former, many more end up the latter, but in this article, we have both, so no one forgets where they came from – or where they’ve ended up.

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16 FAIL: Katherine Heigl

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Katherine Heigl should’ve learned from Mischa Barton: when you have a primo gig, don’t ruin it with your pride. Too bad for the actress, however, who decided to publicly remove herself from Emmy consideration, claiming that she didn’t feel that the material she’d been given that season for Grey’s Anatomy was strong enough to merit a nomination. Then, she badmouthed the hit movie Knocked Up, calling it sexist. The dominos fell, Heigl was removed from the show and neither Shonda Rhimes nor Judd Apatow have had kind words for her ever since.

Clearly, though, Heigl missed the spotlight and tried to get back into Hollywood’s good graces, but her reputation as being difficult to work with meant that her movies flopped and her two TV shows were cancelled after airing only a few episodes. So much for a comeback!

15 SUCCESS: Britney Spears

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She had it all but in 2007, Britney Spears experienced what we think would be considered the worst year of her life. Following her split from Kevin Federline and the removal of her two sons from her custody, Spears went off the deep-end in a public meltdown that saw her shave her head, party excessively, take an umbrella to a paparazzi’s car, and perform an embarrassing routine for the MTV VMAs. It seemed like nothing could pick Spears up from this deep hole she’d fallen into, but it wouldn’t be a comeback if you didn’t hit rock bottom!

By 2008, under the conservatorship of her father (which remains to this day), Spears released the massively successful album Circus, and followed that up with three more albums, including the most recent Glory. She was also tapped to be a judge on The X Factor, with reaction gifs to keep us entertained ever since!

14 FAIL: Lindsay Lohan

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The ultimate failed comeback story, we have Lindsay Lhan, who we will continue to root for and whom, it seems, with continue to fail us.

After finding massive success early on in movies like Mean Girls and Freaky Friday, Lohan fell in with the partying crowd, turned to drug use, volatile relationships, and became a liability on movie sets. Her messy personal life saw her lose out on jobs as she was in and out of courtrooms on a series of charges. Attempting to restart her career multiple times – with 2013’s The Canyons, which flopped, with 2013’s Scary Movie 5, which flopped, and with the TV movie Liz & Dick which, you guessed it, flopped – has proven futile and while we’re still holding out hope that Lohan can turn it around, it seems that her personal demons and changed face will prevent that from ever being the case.

13 SUCCESS: Robert Downey Jr.

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Robert Downey Jr., like the other successful comebacks on this list, enjoyed some success early on, even earning an Academy Award nomination for his titular role in the biopic Chaplin. Unfortunately, his professional success was overshadowed by his personal issues, which included drug abuse and multiple arrests. He lost out on roles and was written out of Ally McBeal for his issues, but it seemed like nothing could stop this train that had gone off the rails.

Finally, in 2003, after spending time in rehab, Downey Jr. tentatively stepped back into the spotlight and nabbed a couple roles in successful films like Good Night and Good Luck and A Scanner Darkly. Eventually, he was cast in 2008’s Iron Man and as a major Marvel success story and bankable actor who is no longer the liability he once was, became the comeback to end all comebacks!

12 FAIL: Sharon Stone

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Sharon Stone, gorgeous and razor-sharp, first won recognition for her role as the ultimate femme fatale in Basic Instinct, which featured that iconic leg-crossing scene. She even had some success afterwards, earning raves for her part in the movie Casino, but then things seemed to fizzle, and no one is entirely sure why, least of all Stone.

Because of that, we can almost understand her decision to attempt to recapture lightening in a bottle by starring in Basic Instinct 2 – 14 years after the original. You can imagine how well that did. The film earned scathing reviews and earned a meager $38.6 million – a tenth of its predecessor. She knew what worked in the past and tried it again, but with lightening, it doesn’t always strike twice, and Stone’s attempt at a comeback collapsed.

11 SUCCESS: Drew Barrymore

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It’s crazy to think that there was a time when the multi-talented Drew Barrymore was anything but a success, but thanks to a rough stint as a childhood actor that later morphed into a battle with substance abuse and a few years as a “wild child”, the actress definitely hit a rock bottom from which it looked like there was no recovery.

After making major waves as cute-as-a-button Gertie in E.T.: The Extra-Terrestrial, Barrymore found herself overworked by her parents, who were addicts themselves, and relied on their daughter to bring in the cash. Barrymore ended up entering rehab at the young age of 13 after experimenting with alcohol, marijuana, and cocaine, and eventually got clean, but her “bad girl” rep stuck into early adulthood, when she finally started earning some big bucks both in front of and behind the camera!

10 FAIL: Ja Rule

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Ja Rule entered the rap scene when it seemed that anyone with a silly name and the ability to rhyme a little could at least score a few hits (thanks, 2000s!). The thing is, Ja was never that good a rapper to begin with, usually relying on collaborations and feature artists to make the charts. In fact, all eight of his Top 10 hits have featured artists! So, it totally makes sense that the mediocre rapper would attempt a comeback as a music festival manager, right?

Yeah, not so much.

In the spring of 2017, we learned of the disastrous Fye Festival, which was founded by Ja and Billy McFarland. The festival promised a luxury experience and people paid tens of thousands of dollars to spent their days on a yacht with models, experiencing the VIP treatment. As we know, things were a colossal failure and Ja hasn’t quite recovered.

9 SUCCESS: Mandy Moore

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Just a few years ago, Mandy Moore would be comfortably situated in the “has been” list of celebrities, but thanks to the massive success of the tearjerker TV show This Is Us, that’s all in the past!

Transforming from a bubblegum pop star who wasn’t quite as famous or successful as her peers like Jessica Simpson, Christina Aguilera, and Britney Spears, Moore found a bit more success than those three in acting, with turns in films like The Princess Diaries, A Walk to Remember, and Saved! Fast-forward to 2010 when she achieved a little more recognition for her work as Rapunzel in the Disney animated feature Tangled, then onto This Is Us and we have a comeback that no one saw coming! Clearly, Moore has her acting skills down – she even nabbed a Golden Globe nomination for her role!

8 FAIL: Mischa Barton

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Mischa Barton was the It Girl of the early 2000s. With her boho chic style and her starring role on one of the hottest shows of the decade – the soapy teen drama The O.C. – it seemed that the world was her oyster.

And then she had the terrible decision to quit in order to move onto bigger and better things.

Instead, she dealt with failed TV shows and low-budget films that didn’t make a dent, critically or commercially, entered and left rehab for drug addiction issues, dealt with mental health and substance abuse, and basically became a mess via her drug-induced self-medication to handle her depression. Choosing to try her hand at Dancing With the Stars, the ultimate comeback vehicle for has-been celebs didn’t work out for Barton, who likely won’t be finding her way back on the A-list anytime soon.

7 SUCCESS: Winona Ryder

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If you were a girl who always considered herself a little bit weird, then Winona Ryder was undoubtedly your favourite actress. Thanks to her parts in off-the-wall films like Beetlejuice and Edward Scissorhands, as well as establishing her indie cred with the classic ‘90s film Reality Bites, Ryder was intelligent and adorable, the pinnacle of the 1990s waif with her big doe eyes and chic hair.

Then, her career came crashing down around her in 2001, when she was arrested for shoplifting. Despite the “Free Winona” T-shirts that became all the rage, Ryder struggled to be embraced back into the Hollywood fold. She had a small part in 2010’s Black Swan as an ageing ballerina, but it wasn’t until Netflix’s Stranger Things – which blended all that Ryder does best: drama, comedy, sci-fi, and ‘80s nostalgia – that she truly got the comeback that she deserved!

6 FAIL: Tara Reid

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The kind of girl every guy had a crush on in the late ‘90s and early ‘00s, thanks to her adorable blonde self in the smash teen series American Pie, Tara Reid seemed poise for great success as a comedic actress. Unfortunately, her party girl antics – combined with some unnecessary (and botched) plastic surgery – put a stop to that real quick.

Reid, instead of finding herself on the red carpet, became a laughingstock and tabloid fixture. Images of her scary-skinny frame, her prematurely aged face, and her incessant partying overshadowed what success she might have had. Even after getting a role in the surprise cult hit Sharknado and its sequels, Reid couldn’t harness the role into other gigs and whatever comeback mojo she might have had has since been wasted – just like her.

5 SUCCESS: Ellen DeGeneres

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It might seem like an alternate universe in which the uber-successful Ellen DeGeneres would have fallen low enough to earn what we call a comeback, but that was actually the case! From 1994 to 1997, DeGeneres had a successful sitcom – the aptly-titled Ellen – but lost it all after publicly coming out (and having her character come out as well) and facing backlash from the public. She attempted to rise from the ashes with another sitcom, this time called The Ellen Show, which was also axed after its first season.

2003, however, was arguably the best year of the comic’s life, as her massively successful talk show premiered, and she lent her voice to the character or Dory in Finding Nemo! With 32 Emmy Awards now under her belt from the show, we’d definitely call that a major comeback!

4 FAIL: Lil Kim

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Another failed comeback story whose waning success might be due to her changing face, we have Lil Kim. When we were first introduced to Lil Kim in the 1990s, she was the kind of over-the-top girl with crazy style and exaggerated figure who could spit rhymes. In fact, its her look that was definitely part of the inspiration behind Nicki Minaj during her Pink Friday era, which is part of what explains the feud between the two back in 2011.

Under Bad Boy Records, Kim found success, but when it started falling, so did she. With this feud with Minaj, Kim could sneak back into the spotlight for her talent, rather than her changing appearance, which has since included accusations of skin bleaching. Unfortunately for Kim, her mix tape“Black Friday” wasn’t as harsh as people wanted and, at $9.99 apiece, simply not worth the money.

3 SUCCESS: Neil Patrick Harris

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Few former child stars have been able to shake off their adolescent past like Neil Patrick Harris, but it didn’t come without a lot of struggle first. After finding success playing the child genius in Doogie Howser M.D. for four years, Harris’s career kind of stalled. Aside from a couple guest spots on other TV shows, it seemed that the child actor was destined to be remembered for that one role, and would fade into obscurity like so many others before him.

In a weird turn of events, though, Harris got a surprise role in the cult hit Harold & Kumar Go To White Castle, playing a womanizing, drug-using, exaggerated version of himself. He stole every scene he was in, landed himself a role on the sitcom How I Met Your Mother – which lasted for nine seasons – and cemented himself as one of the most influential and iconic LGBT actors out there!

2 FAIL: Charlie Sheen

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Charlie Sheen had a lot going on when he went on a massive, public downward spiral in 2011 that saw him giving strange interviews in which he claimed he had “tiger blood” and was living with a bevy of adult film stars, whom he called his “goddesses” We know now that he was dealing with a recent diagnosis of HIV, but at the time, it seemed like an insane drug bender from which there was no return. Sheen lost out on his starring role in Two and a Half Men, for which he was making almost $2 million per episode after badmouthing his boss, and things just haven’t been the same since!

Despite attempting a comeback on the smalls screen with the series Anger Management, the show only managed to last two seasons and doesn’t qualify as the runway success he was probably hoping for.

1 SUCCESS: Martha Stewart

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Who would have imagined that Martha Stewart could go from your mom’s favourite food and home décor celebrity to a bada** 76-year-old who is cohosting a successful TV show with Snoop Dogg of all people?

Now that’s what we call a comeback!

Back in 2004, Stewart was put in the slammer for insider trading but, surprising no one, ended up beloved by the other inmates, putting her true Martha touch on everything in prison. She ended up getting out of the clink in 2005 and returned back better than ever. Instead of appearing holier-than-thou, which was a bit of a turnoff to fans who didn’t feel as picture perfect as the domestic goddess, Stewart had a bit of edge, and seemed to truly enjoy herself. A couple appearances in Comedy Central Roasts, and a fun cameo in Bad Moms, and we have a comeback that is as surprising as it is wonderful!

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