Famed comedian, talk show star, actress and philanthropist Rosie O’Donnell has had an extraordinary career. She’s broken new ground as an openly gay celebrity, contributed many millions of dollars to disaster relief efforts and children’s foundations, and won the nickname of ‘Queen of Nice.’ But she’s also met with controversy over the decades for her political commentary and particularly her feuds with two former presidents.
Here are 20 lesser-known facts about this beloved TV star.
20. She loves Harry Potter so much, she offered to play Molly Weasley for free
By the late 90s, Harry Potter was already one of the biggest and most beloved children’s book series of all time, and had legions of fans eagerly awaiting a film adaptation of the modern classic.
Counted among this group were several celebrity superfans, including Rosie O’Donnell, who had been obsessed with the books ever since their release.
O’Donnell was so obsessed with the series that, when plans of a movie adaptation appeared on the horizon, she personally petitioned Warner Brothers for the opportunity to play a character in the first film.
Specifically, O’Donnell wanted to play Molly Weasley, the loving if sometimes overbearing mother of Harry’s best friend Ron.
Unfortunately for O’Donnell, Warner Brothers had already set their minds on only casting iconic British actors to play major characters in the series, and so she was passed over in favour of British icon Julie Walters.
However, O’Donnell did end up having a cameo of sorts in US editions of the book series, as she provided Molly Weasley’s signature.
19. Her TV special on gay parenting received over 100,000 complaints before it aired
In 2002, O’Donnell appeared on the sitcom Will & Grace, playing the character of a lesbian mother. Later the same year, she officially came out to the public, during a benefit for Ovarian Cancer Research being held at Caroline’s Comedy Club.
O’Donnell clarified in her coming out speech that she didn’t actually understand why a person’s sexual orientation is often considered such a big deal by others, saying: “I don’t know why people make such a big deal about the gay thing… People are confused, they’re shocked like this is a big revelation to somebody.”
O’Donnell’s decision to come out publicly was mostly motivated by a desire to bring awareness to the difficulties that gay parents faced while attempting to adopt children at the time.
O’Donnell’s own experiences with roadblocks as she attempted to navigate the adoption and foster systems as a gay woman led her to be interviewed on PrimeTime Thursday by Diane Sawyer, specifically about the strife that gay parents often faced at that time.
Later, when O’Donnell co-hosted a Nickelodeon special on gay parents in 2002, it attracted a lot of criticism from the Christian group Traditional Values Coalition. According to the Associated Press, the show received over 100,000 complaints via phone and email before broadcast.
This didn’t deter producers, and the episode Nick News Special Edition: My Family Is Different went ahead to critical acclaim. It received an Emmy nomination for Outstanding Children’s Program.
18. She refuses to sign autographs for adults
Some celebrities quickly gain a reputation for being difficult or unaccommodating when it comes to their fans.
With that said, out of all the public figures who have been called out for ungrateful or uncharitable behaviour over the years, Rosie O’Donnell has never really been on that list.
That’s why it’s so surprising to learn that O’Donnell has some pretty strict rules when it comes to how she will engage with fans she bumps into on the street, especially adult ones.
Essentially, O’Donnell has refused to sign autographs for decades, saying in interviews that she just thinks it’s “sad” when anyone asks for the signature of a famous person.
O’Donnell only has one exception to this rule: whenever a child asks her for a photo or autograph in public, she makes sure to always say yes.
It’s a pretty uncommon approach to dealing with the public for sure, but at least she hasn’t left any sad or disappointed children in her wake.
17. She was both prom queen and homecoming queen at school
O’Donnell definitely comes across as a bit of an underdog. She is most famous for playing comedic roles rather than stereotypical leading ladies, and has never been afraid to make fun of herself.
That has led many fans to believe that she must have been unpopular in her younger years, as that’s the story for many famous comedians and actors.
This assumption, that O’Donnell couldn’t have been part of the popular crowd during high school, actually could not be further from the truth.
When she attended Commack High School in New York in the 70s, she was voted senior class president, homecoming queen and prom queen.
However, O’Donnell’s future occupation was predicted by her classmates, as in addition to all her other high school accolades, she was also voted the class clown of her year.
O’Donnell went on to have the ultimate class clown profession, touring as a stand-up comedian for years before appearing in numerous comedies.
16. Madonna is one of her closest friends
Making friends as an actor in the public eye is pretty difficult, which is why so many actors find themselves befriending their co-stars whenever they have a particularly good experience on a film set.
Maybe the most famous example of this is Leonardo DiCaprio and Jonah Hill, who have been fast friends ever since they starred in Django Unchained in 2012.
In a similar situation, Rosie O’Donnell and Madonna have been the best of friends ever since they co-starred in A League of Their Own in 1992.
The friendship has lasted too: this year, Madonna threw a skateboarding-themed 15th birthday party for her daughter Mercy, and O’Donnell was of course in attendance.
O’Donnell has been equally loyal to Madonna, even saying that she would never host Piers Morgan on any of her shows, since Morgan has seemingly had a problem with Madonna for years.
Speaking to Access Hollywood about the feud, O’Donnell said: “He banned Madonna for no reason when his show started, so I’m banning Piers Morgan! I don’t have anybody banned but if I have to make a list, he’s on it.”
15. She was a winning lifeline on Who Wants to Be a Millionaire
Rosie O’Donnell has been a successful comedian and actor for decades, and she hasn’t ever really had to worry about money since the beginnings of her career.
That’s why it might surprise you to know that in 1999, O’Donnell appeared on an episode of the popular game show Who Wants to Be a Millionaire.
O’Donnell wasn’t actually a contestant on the show, but she was on speed dial as one of the lifelines that a contestant could call if they got stuck on a question.
The contestant in question, Jerry Halpin, used his first and second lifelines relatively early in the game, and so only had O’Donnell to call when he found himself unable to answer a question for the third time.
The question that Halpin just couldn’t give the answer to was about Princess Diana, and when O’Donnell answered the phone, she gave him the correct answer effortlessly.
However, she wasn’t totally confident that what she said was correct, as before her it was checked she told Halpin, “If you lose it, the guilt – I’m going to give you the money anyway.” Halpin won $32,000 as a result, and he later appeared on her TV show.
14. She almost had to have her hand amputated
O’Donnell has had a few health troubles over the course of her career. She has openly struggled with seasonal affective disorder for years, and has had serious bouts of depression that have resulted in her temporarily stepping back from public life.
She also suffered a heart attack in 2012, during which her artery was 99% blocked. She was given a stent and pivoted to a whole food and plant-based diet, in order to try and maintain a healthier lifestyle.
Most famously though, O’Donnell experienced a serious staph infection in 2000, after cutting her finger accidentally while taking a price tag off a fishing pole.
She was seriously unwell for weeks, and doctors seriously considered amputating her hand. But O’Donnell recovered from the ordeal, saying afterwards on The View, “I was very lucky.”
O’Donnell maintained a sense of humour throughout the whole ordeal, even jokingly blaming George Bush for her bout of illness.
When questioned about how her staph infection could possibly be the fault of the infamous politician, O’Donnell explained that she had only been purchasing a fishing rod so that she could go fishing during the 2000 Republican National Convention, specifically so she could avoid seeing George Bush on television. Ouch.
13. She has a 2,500-piece collection of Happy Meal toys
Many celebrities indulge a lavish collecting habit, from Angelina Jolie searching the globe for antique knives to Tom Hanks having a whole room in his house dedicated to typewriters.
However, Rosie O’Donnell’s own collecting habit is much less likely to break the bank, as she has pretty inexpensive tastes when it comes to collectables.
As odd as it may sound considering her superstar status, O’Donnell is a dedicated collector of McDonald’s Happy Meal toys, even if the extent of her collection is somewhat accidental.
The walls of O’Donnell’s office are proudly lined with these little plastic toys, which range from tie-in movie promotions to original characters, spanning decades of McDonald’s history.
Her obsession began when she started amassing the 101 Dalmations toys in McDonald’s Happy Meals, enjoying them as a reminder of her childhood.
When McDonald’s heard about their celebrity fan, they sent her the entire range. But O’Donnell didn’t stop there, and went on to collect more than 2,500 Happy Meal toys, which she proudly displays in her office.
12. She was once engaged to a policewoman
Rosie O’Donnell has been in the public eye for a number of decades, and so she’s also had her fair share of relationships beginning and ending in full view of her fans.
However, maybe her most surprising relationship came in 2017, when O’Donnell began a secret, long-distance relationship with police officer Elizabeth Rooney.
Not only was Rooney not a celebrity, but she was also 23 years O’Donnell’s junior, which meant that many eyebrows were raised when the couple went public with their relationship in 2018.
O’Donnell addressed the age difference, as well as the relationship in general in an interview, saying: “I keep telling her I’m too old for her. But she doesn’t seem to care,” she said. “She’s like, ‘I was in the Army! I put my life on the line every day you think I don’t know who I want to date?’ I’m like, ‘All right I guess that’s true.’ She has a lot of good points.”
Unfortunately, the pressures of dating a celebrity while also attempting to navigate a normal job and life proved too much for Rooney, and the pair broke off their engagement after less than a year.
O’Donnell spoke about the relationship in the aftermath of their breakup, saying: “We are still figuring things out – it’s hard in the public light.”
11. She published a book of children’s jokes sent to her by young fans
Throughout her life and career, Rosie O’Donnell has always had a pretty good relationship with her young fans, and has even made content specifically for them over the years.
In 1997, O’Donnell published a book called Kids are Punny: Jokes Sent by Kids to the Rosie O’Donnell Show, which lists a selection of the greatest quips from her younger fans.
Just one year later in 1998, a sequel to the book was released, called Kids are Punny 2: More Jokes Sent by Kids to the Rosie O’Donnell Show.
The two books were even so popular that they were adapted into an HBO television special, which featured numerous celebrities from Madonna to Gilbert Gottfried.
The two pun books were Rosie O’Donnell’s first but not only foray into literature, as later in 2002 she released Find Me, a combination of mystery, detective story and memoir.
The book reached number two on the New York Times bestseller list, and delved into her relationships with women, as well as her childhood and early adulthood experiences.
10. She got married as a show of defiance to George Bush
Rosie O’Donnell was definitely in love with Nickelodeon executive Kelli Carpenter when the two decided to tie the knot in 2004, but their marriage was about more than just celebrating their relationship.
A significant part of their decision to get married was a desire on O’Donnell’s part to stick it to President George Bush, who she had vocally spoken out about on a number of previous occasions.
Carpenter and O’Donnell got married in San Francisco, just two weeks after Mayor Gavin Newsom announced that he would allow the granting of marriage licences to same-sex couples.
At the time, President Bush was supporting the Federal Marriage Amendment, leading many LGBTQ+ couples to get married in San Francisco in a show of rebellion and solidarity.
O’Donnell later said of her decision to get married: “We were both inspired to come here after the sitting President made the vile and hateful comments he made … One thought ran through my mind on the plane out here – with liberty and justice for all.”
Sadly, the marriage was annulled just a few months later along with those of thousands of other couples who also took advantage of the San Fransisco marriage licences.
9. She attended Donald Trump’s second wedding
Rosie O’Donnell has had a contentious relationship with Republican politicians over the years, having very publically feuded with George Bush throughout his presidency.
O’Donnell kept this energy when Donald Trump ran for President, frequently voicing her opposition to him while holding the chair as moderator of The Voice talk show.
It’s not difficult to imagine why Donald Trump and Rosie O’Donnell would be at odds with each other, especially given their diametrically opposed viewpoints on most political issues.
What is surprising is that there was a time when the pair were far from enemies, and were instead even friendly enough to run in the same New York entertainment circles.
Most surprising of all is the fact that when Donald Trump married his second wife, actress Marla Maples, in 1993, O’Donnell was invited to the ceremony.
O’Donnell attended the wedding but soured on the couple sometime later, or at the very least revealed her true feelings towards the real estate mogul and politician.
8. She dropped out of university twice
We’ve already discussed the fact that Rosie O’Donnell, contrary to many other actors, comedians and performers, had essentially the perfect high school experience.
She was beloved by her classmates, popular enough to be crowned both prom and homecoming queen, and gained a reputation as a funny and likeable person to work with.
Unfortunately for O’Donnell, her picture-perfect record did not continue once she graduated high school and headed to college.
In 1980, O’Donnell first headed to the private liberal arts college Dickinson College in Pennsylvania, but she ended up attending classes there for less than a year.
O’Donnell then transferred to Boston University and intended to finish up her courseload there, but she dropped out of college altogether not long after.
Thankfully, her decision to start paying her dues on the comedy circuit sooner rather than later paid off, and she was able to build a successful career for herself relatively early on.
7. She has said she will never have biological children
As well as balancing a successful acting career with time working as a comedian and talk show host, O’Donnell has also had to make time for raising a family.
O’Donnell has never shied away from the fact that she has always wanted children, and that they are a significant part of her life, despite the difficulties gay parents faced in the adoption system when she first began considering the option.
The third of five children herself, Rosie O’Donnell adopted her first child, Parker Jaren O’Donnell, when he was an infant in 1995.
O’Donnell raised him as a single parent, until she married Kell Carpenter in 2004. The pair have four children together, and began fostering a girl named Mia in 2000, who they had planned to adopt.
O’Donnell and Carpenter began living separately in 2007 and, because their marriage was annulled by the California Supreme Court just months after the ceremony, a legal divorce was made unnecessary.
O’Donnell got engaged to executive consultant Michelle Rounds in 2011, and the pair adopted a baby named Dakota in 2015.
6. She turned down Hocus Pocus thinking it would be “too obnoxious”
Hocus Pocus was released in the summer of 1993, and ever since then, it has been a Halloween staple, beloved by generations of kids.
As well as Winnifred’s iconic dress becoming one of the most popular Halloween costumes on the market, the film also spawned an extremely successful Walt Disney World castle show, and a long-awaited sequel has even been announced for 2022.
Since Hocus Pocus is now such an ingrained part of pop culture, it can be difficult to imagine anyone else in the roles of the witches, besides Bette Midler, Sarah Jessica Parker or Kathy Najimy.
However, Najimy wasn’t even the casting director’s first choice for the role, as pretty much everyone agreed that Rosie O’Donnell would bring the exact right energy to the character.
O’Donnell turned down the role immediately, and the reason why might surprise you: she actually thought that any version of the character would have been “too obnoxious” for her.
O’Donnell’s unwillingness to appear in Hocus Pocus did not translate into a dislike of Disney on the whole though, as she did later voice the character of Terk the gorilla in Tarzan.
5. She had no idea best friend Nora Ephron was sick
Rosie O’Donnell’s decades in the world of entertainment means that she has cultivated friendships with a fair few famous figures.
Her most famous celebrity friendship is obviously that she shares with Madonna, but O’Donnell also considered legendary filmmaker and journalist Nora Ephron amongst her close friends.
Sadly, Ephron passed away in 2012 at the age of 71 from leukaemia, a diagnosis that she kept secret from both the press and her real-life friends.
As a result, most of her close friends had no idea that she was sick, and O’Donnell was amongst those who were shocked by Ephron’s passing.
In 2015, Ephron’s son Jacob Bernstein released a documentary called Everything is Copy, which explored Ephron’s life and work.
Rosie O’Donnell was one of numerous celebrities who appeared in the film, in order to talk about Ephron, her legacy, and the impact she had on her friends.
4. Her second wife took her own life
O’Donnell began dating Michelle Rounds in the summer of 2011, and by December of that same year, O’Donnell announced to the world that the pair were engaged.
The two got married in a small, private ceremony in New York on the 9th of June 2012. The next year, in 2013, the newlyweds announced that they were adopting a baby girl named Dakota.
The executive-search consultant and O’Donnell seemed very happy together, but in 2015 it was announced that the couple were no longer together.
Not only that, but the pair had actually functionally separated in the winter of 2014, but had attempted to keep the news out of the press.
The divorce was finalised and settled in October 2015, during which time it was announced that O’Donnell would have full custody of their adopted child Dakota.
Two years later, in 2017, Michelle Rounds was discovered to have tragically died of suicide, with the reasons being unknown.
3. Her eldest daughter went missing in 2015
Chelsea Belle O’Donnell is the eldest daughter of Rosie O’Donnell and Kelli Carpenter, a former executive notable for working at Nickelodeon.
Chelsea was born in 1997, and was adopted by O’Donnell and Carpenter after they got married in 2004, making her the second child to be adopted by O’Donnell.
O’Donnell already had experience raising adopted children, since she had been raising Parker Jaren O’Donnell by herself, since adopting him as an infant in 1995.
However, just like any relationship between a child and their celebrity parent, O’Donnell and Chelsea Belle did experience some difficulties.
In 2015, when Chelsea Belle was nearly 18 years old, O’Donnell tweeted that her daughter had gone missing from her home.
It later transpired that Chelsea Belle had run away from her home, along with her service dog Bear, but she was located safely a week later in New Jersey.
2. She was critiqued for her vocal love of Tom Cruise
O’Donnell has proudly identified as a lesbian ever since coming out in 2002, which has occasionally led to protest groups objecting to her appearance on certain TV shows, or her willingness to talk about certain topics.
That kind of backlash was to some degree expected, but she was surprised when she also came under fire for precisely the opposite reason.
For years, Rosie O’Donnell has had a running joke centred on her obsession with famous actor Tom Cruise, who she has professed to find super attractive.
Over the years, she has made jokes about keeping Tom Cruise around as her personal housekeeper, in order to watch him clean her pool or do other chores.
Despite very obviously being a tongue-in-cheek bit that was not meant to be taken seriously, many LGBT groups said that her comments about Tom Cruise were deceptive.
Rosie O’Donnell responded to her critics directly, saying: “I said I wanted him to mow my lawn and bring me a lemonade. I never said I wanted to blow him.”
1. She almost starred in Agnes Browne
If you’ve never heard of the 1999 film Agnes Brown, don’t worry, you’re not the only one. The movie received a dismal reception from America when it was released, and it did not receive much more praise in Britain.
It follows the struggles of the titular character, who attempts to keep herself and her seven children above water in the face of financial hardships, loans sharks and a deep desire to attend a Tom Jones concert.
The film was a passion project of actor Anjelica Huston, who starred in, directed and produced the movie all by herself, after reading and being inspired by the book it was based on.
Huston obviously had significant sway when it came to making casting decisions, and there was only one actress she could picture in the role of happy-go-lucky friend Marion: Rosie O’Donnell.
The character of Marion seemed like a perfect fit for the mix of comedy, sentimentality and reliability often present in O’Donnell’s work, and so Huston reached out to O’Donnell and asked her if she would consider appearing in the project. O’Donnell turned the part down outright, but not because she had any idea of how badly the film would be received. Instead, the production was set to begin shortly after the tragedy of the Columbine Massacre, and O’Donnell felt she was just too emotional to take on any new work.