What can be said about former talk show host Rosie O’Donnell in the year 2018? Well, though I don’t intend to insult any stalwart Rosie fans out there, I think we can all collectively admit that she is far past her prime. While other late night personalities and media moguls go on to age gracefully and retire with their integrity intact, that doesn’t seem to be the path poor Rosie has taken. She’s been at the center of celebrity familial turmoil, health crises, and political upheaval, and it’s all left a mark on the once-popular comedian/activist.
A major fixture of turn-of-the-century media, The Rosie O’Donnell Show was at one time popular enough to contend with the likes of morning talk shows like Sports Center and even Today, but that’s a difficult realm in which to compete, and the show’s tenure would eventually wane and come to an end in 2002.
Though the show was fairly lighthearted and featured softball topics like broadway shows and charitable work, Rosie became something of a counter-culture icon in later years. Earning a status as an against-the-grain progressive mind and developing a contentious feud with a certain New York businessman who would go on to become the President of the United States, O’Donnell seems to have nearly collapsed beneath the weight of her own popularity, and, as a result, Hollywood doesn’t want anything to do with her these days. She has tried to make a comeback in recent years, but it’s difficult to tell what the future holds for her.
15 She Left At the wrong time
Rosie O’donnell used to be everywhere: from a morning talk show to appearances on Broadway to taking to the seas in her own cruise line, it’s mind boggling to think that we live in a time in which she has, by comparison, seemingly been forgotten. She was, at one time, the host of the highest rated talk show in North America, which is absolutely no small feet. In an industry with competitors which have been around since nearly the inception of the medium itself, rising to the top in a few short years is beyond impressive.
Unfortunately, Rosie pulled the plug on the show in 2000 when she announced that she would not renew her contract. Citing an interest in pursuing family matters and increasing her charitable efforts, the show would continue on until it was finally brought to an end in 2002. An absolute staple of late '90s television, Rosie used to fill the role currently occupied by people like Savannah Guthrie and Hoda Kotb. Would her career in television have stayed the course had she not given it up nearly one and a half decades ago? Nobody can know for sure, but I would imagine that she would still be a much bigger name today had she not walked away from it all at such a crucial moment.
14 She Engages in Public Feuds with Her Daughter
I’ll admit that I wasn’t even aware that Rosie O’Donnell had a daughter until recently. The ex-talk show host has engaged in some relatively a-typical relationships over the years, so it may come as a surprise to some to see that she actually does have a daughter. Unfortunately, the two aren’t exactly close. They often get into very public feuds, and neither of the two appear to have anything particularly polite to say about the other. Thanks to this, Rosie has earned a reputation as a bit of a home-wrecker, though her daughter seems to also be somewhat rough around the edges.
This bad blood was outed when, in August of 2015, Chelsea actually ran away from home at the age of 17 and spent a week AWOL at an apparent lover's house. The whole thing resulted in a legal struggle and a media field day, and, given that she had also recently departed from The View, things weren’t exactly looking up for O’Donnell. Rosie’s daughter was said to have been suffering through mental illness which served as the impetus for her actions, but the rift between mother and daughter has yet to heal nearly three years later, and Chelsea’s recent pregnancy announcement has only made things worse.
13 She Tells It Like It Is
Rosie used to garner the adoration of the nine-to-fivers who watched her show in the late '90s because she had a reputation for delivering her unfiltered, real opinions. Unlike some other A.M. programs which often spent time covering downy topics and going over fluff pieces, O’Donnell was thought of as a renegade who offered her unfiltered thoughts for better or, far more often, for worse. Within the context, though, it was a respectable trait, and most audiences were happy to see an anchor who didn’t seem encumbered by a litany of teleprompters and pre-written sets of dialogue.
It was, however, a reputation which came back to bite her. Rosie was notorious for scarring away advertisers and alienating some subsections of her viewer base. Once her material became a bit harsher, her ratings began to drop, and it became clear that America wasn’t quite ready for the likes of Rosie O’Donnell. Perhaps she was a bit ahead of her time, or perhaps she really was a bit to abrasive for a coffee-sipping, get-the-kids-to-soccer-practice crowd. Either way, it only helped to accelerate her acceptance from Hollywood. Sure, she pops up now and again, but she is nowhere near where she was during the height of her popularity.
12 She May not have been the best mom to her daughter
On the heels of the news that Chelsea, Rosie’s daughter, was pregnant came a flurry of back-and-forth accusations between the estranged family members. O’Donnell has never seemingly had anything good to say about her daughter, but things really became heated when, in May of 2017, Chelsea accused her mother of mistreatment.
“A couple of weeks prior, I had gotten a tattoo. [Rosie] had spyware on my phone so she could see pretty much everything I did. She called me into her room and asked me about the tattoo. I denied it.
She asked me to [show her],” Chelsea relayed in an interview last year. “She picked up a bottle and started chasing me.” Not exactly the greatest mother-daughter dynamic, but Rosie’s point of view could perhaps be understandable were we to hear it from her side. No parent is likely to approve of their young daughter getting a tattoo, but a monitoring her phone does seem a little bit extreme. Either way, it wasn’t really a good look for either of them, and though the accusations are unfounded, it’s a wrap that O’Donnell hasn’t entirely managed to shake.
11 The World of Politics Hasn’t Been Good to Her
We’re all very aware of the not-so-nice feud between Rosie and the current President of the United States which has seemingly been going on forever. The President has never been a fan of O’Donnell, and he even made a point of insulting her during a debate during the 2016 Republican primary.
This long-standing disagreement actually has roots which can be traced back more than a decade. In 2006, the pre-presidential candidate and co-owner of the Miss Universe pageant announced that he would be giving pageant candidate Tara Conner a second chance after allegations of her substance use came to light. Rosie, who was, at the time, a major fixture of the popular talk show The View disavowed the move and went on a tirade against the billionaire businessman. The pageant owner fired back, calling Rosie a “woman out of control,” and the argument continued to spiral out of control and grow to such massive proportions as to eclipse the actual origins of the fighting. I doubt that either of the two actually remember how this all started, and, at this point, it seems like a major pillar in the natural order of the universe that Rosie O’Donnell must dislike a certain New York businessman turned politician.
10 She Didn’t Fit In Well at The View
Following her exit from the show which bore her name, Rosie O’Donnell found a place for herself for years later as a part of the Barbara Walters-led morning talk show, The View. Though her public notoriety had died down somewhat since her days of hosting The Rosie O’Donnell Show, she was, at that time, a welcome addition to the program.
Talk shows thrive on the chemistry between co-hosts, however, and it became apparent early on that O’Donnell was something of a fly in the ointment for her cast mates. O’Donnell allegedly often fought with co-star Whoopi Goldberg, and she apparently disliked her one-sided viewpoints concerning many topics. That came to a head, when news broke of comedian Bill Cosby’s illicit and non-consensual relations with women, and it really left a sour taste in the mouths of producers and viewers of the show alike. O’Donnell was also know to butt heads with the likes of Elisabeth Hasselbeck, with whom she feuded over the state of the Iraq War, and Rosie Perez, with whom she argued over practically everything. O’Donnell may have been a seasoned talk show veteran and professional newscaster, but, as time went on, it became increasingly obvious that The View just wasn’t the place for her.
9 She was Sued by One of The View’s Producers
Not only did she have beef with many of her co-stars on The View, but she drew the ire of more than a few of the show’s production crew. In 2015, an altercation between Rosie and Jennifer Shepard-Brookman, one of the View’s top producers and a veteran of ABC, became so virulent that the incident had to be reported to the network’s human resources department. In the wake of that altercation, Shepard-Brookman was fired, and the show continued on with Rosie O’Donnell until she walked away from the program later that same year.
That wasn’t the end of things, however, as Shepard-Brookman, who believed herself to be the victim of Rosie’s tyrannical nature and ill temper, filed a lawsuit against her in 2015.
This unearthed a slew of allegations and awful goings-on behind the scenes, and it outed the fact that Rosie was actually nicknamed “The Beast” by some of the show’s crew thanks to her contemptible behavior. Reputations of that nature are not easy to shake, and it’s little wonder that, following an altercation as fiery as this, executives in Tinsel Town aren’t eager to bring Rosie O’Donnell aboard any upcoming projects. She may have been a darling of the late '90s and early 2000s, but her sterling reputation has since been tarnished.
8 Oprah Winfrey Backed The Rosie Show, But It Flopped
When Oprah Winfrey departed her famous talk show in 2011, it was major news. While she went on to found The Oprah Winfrey Network, often shortened to just OWN, it hardly helped to fill the gap left in TV land created by her departure. Though the network is still around, it rarely makes much of an impact, and there’s hardly anything of impact or importance going on over there.
In 2011, the same year as the network’s creation, it was announced that Rosie O’donnell would be getting her own slot on the network’s scheduling with The Rosie Show. Fans were hopeful that it would be a return to form following the talent’s nine year absence from a self-titled morning talk show vehicle, but, when it debuted a year later, it was pretty obvious that the production would be a far cry from Rosie’s glory days.
The Rosie Show went on to suffer from miserable ratings and was canned after a short six month stint on Oprah’s new network. Rosie had already earned a reputation for toxicity in the work environment, but not even a crew of talented professionals and an audience of like-minded individuals could save the production. She would continue her work on The View for a few more years before she folded from that as well.
7 She had a ton of Health Issues
When word spread that Rosie O’Donnell would finally be departing from the view in early 2015, many speculated that her health may have been in jeopardy. Unfortunately, she partially confirmed those suspicions by stating in an interview that a series of ailments had played a part in her decision to part from the program.
"[My health] got a little bit worse right before the holidays,” she said. “[my doctor] was kind of concerned.”
The stress of the show had apparently become an issue, and it’s yet another reason why network executives might think twice before casting Rosie O’Donnell in anything or signing her to a long-term contract. O’Donnell also suffered a heart attack in 2012, which left her in an ailing condition and caused panic and grief across the Rosie-verse. The talk show host admitted to feeling all of the symptoms of a heart attack at the time, though she didn’t quite understand what was happening and ended up only going to see a doctor the following day. She's stated that she counts herself as “one of the lucky ones,” and has acknowledged that situations such as hers are very often life-threatening. Fortunately for her fans, she managed to endure the medical crisis and continued on with her professional activities.
6 She’s Been A Part of Some Weird Relationships
O’Donnell made waves when she revealed her previously unknown marital preferences in 2002. Since then, her status as a family-friendly talk show host has been a bit contentious, and the relationships in which she has since engaged have been troubled to say the least. Twice divorced, Rosie has become pretty notorious for her inability to keep her romantic life together, and, while plenty of celebrities in similar situations go through marriages like it’s nothing — Larry King has been married about half a million times — it’s a wrap that really sticks to her.
Perhaps it’s a prevalent subject as a result of the unfortunate passing of Michelle Rounds, her ex-wife whom she divorced in 2015. If you haven’t noticed, 2015 was not a good year for O’Donnell, though few recent years have been particularly kind to her. The two were only married for a short three years and dated for only four, but the 2015 divorce was actually the result of months of marital strife and a struggle to maintain custody of an infant the couple had adopted in 2013. It’s safe to say that little has gone Rosie’s way recently, but this public image disaster definitely hasn’t helped her land any new gigs.
5 “The Man” Has Got Her Down
Political strife is nothing new to the hills of Hollywood, and plenty of film and television stars are very blatantly displeased with the country’s current leadership. While such a partisan issue is better left for discussion elsewhere, it is safe to say that we are all extremely aware of the direction in which Rosie O’Donnell’s political compass points. She almost certainly would not have been allowed on The View were she not as outspoken about her particular set of beliefs as she is, but she has stated that, ever since the election of a certain blonde businessman with whom she has publicly feuded for years, she has stated that she has been in a state of “severe depression” and that she spends “90 percent of her waking hours tweeting hatred” at the current political situation. Not a particularly great spot to be in, but there’s doubtlessly more than a few shoulders in Tinsel Town on which she could cry.
That said, she’s become the poster child for the anti-Republican sentiment currently brewing among certain political circles, and, though it is an upside to some, that kind of baggage makes it difficult for her to be cast in non-partisan roles. If Rosie joins a show, we’ll be able to take a very accurate guess at the program’s political leanings.
4 She Was Sued By the Publisher of Her Magazine
Does anyone remember Rosie Magazine? Chances are that few do: it was a pretty short lived publication which folded in tandem with the end of The Rosie O’Donnell Show in 2002. It may seem kind of insane today to think that O’Donnell may think of putting her own magazine out there, but her profile was so much higher back then that anything seemed possible for her. Rosie walked away from the production in mid-2002 to coincide with her apparent exit from all things media, but doing so resulted in a drawn out legal battle. The mag’s publisher, Gruner + Jahr USA, claimed that her departure was a breach of contract, and she was sued for a staggering $100 million.
O’Donnell, in perfect Rosie fashion, countersued for an equally astounding $125 million, citing that she was left out of key editorial decisions and wasn’t allowed the kind of control she would have liked.
In the end, a judge ruled that neither party deserved reparation for damages in the wake of Rosie’s exit from her eponymous publication. It was a media frenzy at the time, though the whole thing ultimately led nowhere. It did, however, remind entertainment moguls to be mindful of O’Donnell and her apparently vicious nature.
3 Rosie Meddled
O’Donnell has made herself out to be a bit of a maniac recently on Twitter: she’s gone on long streaks of ranting and raving about the current political climate, and she’s done and said more than a few things that I’m assuming she would like to take back.
In the midst of her grilling of the proposed Republican tax overhaul of 2017, O’Donnell pledged that she would shell out a total of $4 million to a pair of U.S. senators if they elected to vote against the tax plan. Her plans fell through, and neither of the senators actually took Rosie up on her offer.
Both Senator Susan Collins of Maine and Senator Jeff Flake of Arizona voted in support of the Republican tax plan, and O’Donnell was subsequently berated on Twitter for her attempted meddling. While I admittedly know little about political machinations, I’m pretty sure that it’s illegal to bribe politicians, and it’s sort of a wonder that this instance didn’t result in any legal attention. O’Donnell may not have been serious about her offer, but, given her status as a political activist, that might be the type of mystery which won’t easily be solved.
2 Her divorces weren't easy
I’ve already spoken about Rosie’s unfortunate marital dealings, and we are all grimly aware that, when it comes to romance, hardly anything she touches ends up bearing fruit. This may not exactly be surprising given her bullish reputation, but it’s actually a bit astonishing to see just how thoroughly she’s managed to damage the relationships of others.
She’s alleged to have had a relationship with broadway actress Dana Caruso Schiff, and the whole thing led to Schiff’s divorce and custody battle with her ex-husband, David Schiff. None of this is a good luck for Rosie O’Donnell, who has famously been lauded for her treatment of her late ex-wife Michelle Rounds. They went through a bit of a nasty divorce and an even nastier custody battle back in 2015, and it almost hurts to see that she’s kept that going, albeit with another couple.
She’s also disrupted the stability of her own home. I’ve mentioned it already, but Chelsea, her daughter, clearly didn’t take kind to living in her mother’s home, as she ran away at the age of 17 and spent a week with a lover. Some never really take to being the head of a household, but it seems that the ex-talk show host and comedian really has a penchant for messing things up when it comes to family stability.
1 She doesn't hold back
A controversial figure since the end of her eponymous '90s talk show, Rosie O’Donnell is perhaps most famous, or infamous, for a slew of controversial remarks she has made throughout the years. From derogatory and insensitive comments about the U.S. military to expressing her strange views on the recent Bill Cosby case, it is safe to say that her fellow co-stars must feel a bit anxious whenever she is around a live mic.
Be it in interviews or on live, heated debates on TV, she really doesn't seem to have much of a filter, which makes her involvement in some projects downright dangerous.
In 2011, she criticized the casting direction of the at-the-time famous prime-time musical production Glee by controversially remarking that “pretty, heavy girl,” essentially saying that she didn’t think actress Ashley Fink was attractive enough for the role. She also slammed President Obama for opting to do an interview on The View during his 2012 re-election bid, a move which drew the ire of many of her political bedfellows. Most controversially, in a 2007 episode of The View, she essentially commented that she thought the U.S. military to be the real bad guys of the then-ongoing Iraq War. This comment was poorly received by those on both sides of the isle, and it’s made her out to seem obnoxious and insensitive to some.
References: businessinsider.com, pagesix.com, thewrap.com, cbsnew.com