| # | Fact |
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| 1 | Has her own company Flower Films which discovered the script of 50 First Dates (2004) and that this had been optioned by Adam Sandler's company. Having enjoyed working with him on The Wedding Singer (1998), she immediately wanted to be involved with him on this. |
| 2 | On April 1, 2016, this was reported that she had separated from her third husband of 3 years Will Kopelman, and on July 15, she filed for divorce from him. |
| 3 | Named after her great-grandparents, Georgiana Emma Drew and Maurice Barrymore (whose actual name was Herbert Arthur Chamberlayne Blythe), both were American stage actors. |
| 4 | Returned to work 5 months after giving birth to her daughter Frankie to begin filming Miss You Already (2015). |
| 5 | Both her Grandfather John Barrymore and Great Grandfather Maurice Costello have played the role of Sherlock Holmes, with Maurice being the first recorded actor to do so. |
| 6 | Her roommate at age 13 in Los Angeles was actress Ele Keats. |
| 7 | Sister-in-law of Antonio Gioffredi (Dolores' husband). Aunt of Gabriella and Nicole Gioffredi. |
| 8 | Was 2 months pregnant with her daughter Frankie when she completed filming Blended (2014). |
| 9 | Gave birth to her second child at age 39, a daughter named Frankie Barrymore Kopelman on April 22, 2014. Child's father is her now estranged third husband, Will Kopelman. |
| 10 | Returned to work 8 months after giving birth to her daughter Olive to begin filming Blended (2014). |
| 11 | (June 2, 2012) Married for the third time her boyfriend of 16 months Will Kopelman following a 5-month-long engagement. Among the guests were Steven Spielberg, Reese Witherspoon, Naomi Pomeroy and Busy Philipps. Best friend Cameron Diaz served as maid of honor. The reception was catered by Vinny Dotolo and Jon Shook. Wedding planner was Yifat Oren. |
| 12 | Confirmed her engagement to art consultant Will Kopelman, whom she has been in a relationship with since February 2011, after he proposed to her with a colorless 4-carat diamond engagement ring on vacation in Sun Valley, Idaho (January 5, 2012). |
| 13 | She was awarded a Star on the Hollywood Walk of Fame at 6925 Hollywood Boulevard in Hollywood, California on February 3, 2004. |
| 14 | Received her first kiss from Breckin Meyer, when they were both in grade school (she was 10 and he was 11). |
| 15 | Was set to play the lead in Gregg Araki's "Frigid & Impotent" (1996). This project never happened. |
| 16 | Auditioned for Heathers (1988), Great Balls of Fire! (1989), Cry-Baby (1990), Edward Scissorhands (1990), Bram Stoker's Dracula (1992) and Cape Fear (1991). Four roles were lost to Winona Ryder. |
| 17 | Ex-daughter-in-law of Mary Jane Green and Richard Green. |
| 18 | Gave birth to her first child at age 37, a daughter named Olive Barrymore Kopelman on September 26, 2012. Child's father is her now estranged third husband, Will Kopelman. |
| 19 | Aunt of John Blyth Barrymore IV, Sabrina Brooke and Blyth Lane Barrymore. |
| 20 | Has starred alongside Adam Sandler in three movies: The Wedding Singer (1998), 50 First Dates (2004) and Blended (2014). |
| 21 | Was named "Stonette of the Year" by High Times magazine in 2010 (for her performance in Going the Distance (2010)). |
| 22 | Was in consideration for the role of Joyce Lakeland in The Killer Inside Me (2010), but Jessica Alba was cast instead. |
| 23 | During a 1995 appearance on Late Show with David Letterman (1993), Barrymore shocked the normally unflappable host by climbing onto his desk and flashing him (but with her back to the camera) for his birthday. |
| 24 | Former sister-in-law of Jacqueline Barrymore and Rebecca Pogrow. |
| 25 | Was in consideration for the role of Sandra Dee in Beyond the Sea (2004), but Kate Bosworth was cast instead. |
| 26 | Was in consideration for the role of Brandon Teena in Boys Don't Cry (1999). However, Hilary Swank, who went on to win the Best Actress Oscar for her performance, was cast instead. |
| 27 | Auditioned for the role of Satine in Moulin Rouge! (2001). However, Nicole Kidman, who went on to receive a Best Actress Oscar nomination for her performance, was cast instead. |
| 28 | Referenced in the Tim Sandlin book "Jimi Hendrix Turns Eighty" as the future governor of California. |
| 29 | Was in a relationship with Justin Long twice. Their first relationship lasted from August 2007 until July 2008, and then in June 2009 they reconciled following a trip to Disneyland. They began living together in August 2009 but later broke up in November 2009. |
| 30 | EdenPark, a punk band from York, Pennsylvania, recorded a song called "Barry Loves Drew Barrymore" on their limited edition, 2002 vinyl release, "Journey to the Center of Skull Mountain". |
| 31 | Referenced by name in the movie Monkeyshine (2008). |
| 32 | Ranked #40 on Maxim magazine's Hot 100 Women of 2008 list. |
| 33 | Close friends with Nancy Juvonen. She and Nancy have a production company together called Flower Films. |
| 34 | Great-granddaughter of Maurice Barrymore and Georgiana Barrymore. Great-great granddaughter of Louisa Drew. Great-grandniece of Sidney Drew. Grandniece of S. Rankin Drew, Ethel Colt, John Drew Colt and Samuel Colt. |
| 35 | On October 10, 2009, she became the most frequent reoccurring female host of Saturday Night Live (1975), to date, hosting for her sixth time. |
| 36 | Was named as an Ambassador Against Hunger for the United Nations World Food Program. [2007] |
| 37 | Is a huge fan of The Beach Boys and appeared in their music video, "Rock and Roll to the Rescue" as well as singing "Wouldn't It Be Nice" in the film 50 First Dates (2004). Other favorite musicians include: The Beatles, Daft Punk, Lauryn Hill, Coldplay, Ratt and Beck. |
| 38 | Her godfather Steven Spielberg is also the godfather of Gwyneth Paltrow. |
| 39 | Was ranked #3 in E's 50 cutest child stars all grown-up. [2005] |
| 40 | Personal assistant is Kelly Kall. |
| 41 | Ranked #5 in VH1's list of the "100 Greatest Kid Stars". |
| 42 | When she found out that a 23-year-old girl wanted to be on MTV's I Want a Famous Face (2004) and have cosmetic surgery to look like her, she contacted the girl and successfully convinced her to not have the surgery. |
| 43 | Currently (2005) resides part time in Hollywood Hills, California and part time in Manhattan, New York City. |
| 44 | Best friends with Cameron Diaz since Charlie's Angels (2000). Both Cameron and Drew are huge fans of the heavy metal group Ratt. |
| 45 | She was delivered by Dr. Paul Fleiss, father of Heidi Fleiss. |
| 46 | Her first of two impulsive marriages was to Welsh-born Jeremy Thomas, who was a Los Angeles barkeep. They had known each other only six weeks before they married, which was decided within hours one night. The impromptu setting was at Thomas' bar, "The Room", on Cahuenga Boulevard, shortly after 5:00 a.m, on March 20, 1994. Supposedly both were sober. The minister was a clairvoyant from a psychic hotline who arrived within a half an hour after being paged. |
| 47 | Became a huge fan of the Boston Red Sox during the filming of the movie Fever Pitch (2005). |
| 48 | Resided with David Crosby and his wife for over a year. |
| 49 | She is allergic to garlic, bee stings, perfume and coffee. |
| 50 | One of her hobbies is photography. |
| 51 | Referenced by name in the Invertigo song "Typical". |
| 52 | Godmother of the late Kurt Cobain and Courtney Love's daughter, Frances Bean. |
| 53 | Was in a long-term relationship with The Strokes drummer, Fabrizio Moretti (June 2002-December 2006). |
| 54 | Received a star on the Hollywood Walk of Fame on February 3, 2004, joining her famous relatives Ethel Barrymore, John Barrymore and Lionel Barrymore as recipients of that honour. |
| 55 | In honour of Bill Clinton turning 50, John Kennedy Jr. had Drew pose as Marilyn Monroe on the cover of his magazine, "George", with the heading, "Happy Birthday, Mr. President", which Marilyn Monroe sang to his father at the now-infamous May 19, 1962 birthday salute to President John F. Kennedy. [September 1996] |
| 56 | Ranked #61 in Premiere magazine's annual Power 100 List (2001). |
| 57 | Married Tom Green twice: first eloping to the South Pacific in March 2001, then on July 7, 2001 before family and friends in a ceremony in Malibu, California. She and Tom Green then honeymooned in Ireland. |
| 58 | Began a relationship with Tom Green in February 2000, before getting engaged to him in July 2000. They married on July 7, 2001, but separated in December 2001 after just five months of marriage. Their divorce was finalized in October 2002. |
| 59 | In 1990, at the time completing her autobiographic book titled "Little Girl Lost" she was age 14. |
| 60 | During an appearance on The Rosie O'Donnell Show (1996), she said that she never watches any of the movies she stars in. |
| 61 | Her $3-million Beverly Hills mansion caught fire while she and fiance Tom Green were inside sleeping. The couple succeeded safely out, but the house was ruined. [February 2001] |
| 62 | Was offered the leading role of Nomi Malone in Showgirls (1995), which she turned down because she felt uncomfortable with the explicit nudity displayed in the script. |
| 63 | She was formerly a vegan: "I don't eat a ton of meat, and I don't wear a ton of leather, but I just don't put strict limitations on myself anymore.". |
| 64 | As a child, she auditioned for the role of Carol Ann Freeling in Poltergeist (1982), which went to the late Heather O'Rourke. |
| 65 | Her godmothers are Sophia Loren and Anna Strasberg. |
| 66 | Her favorite poet is e.e. cummings. |
| 67 | Steven Spielberg gave her a quilt for her birthday with a note "Cover yourself up". Enclosed was a copy of the January 1995 issue of Playboy Magazine for which she posed nude, with the pictures altered by Spielberg's art department so that she appeared fully clothed. |
| 68 | Listed as one of twelve "Promising New Actors of 1984" in John Willis' Screen World, Vol. 36. [1984] |
| 69 | Her father had English, Irish, and German ancestry, and her mother is of Hungarian descent. |
| 70 | Daughter of John Drew Barrymore and Jaid Barrymore. Half-sister of Jessica, Blyth Dolores and John Blyth Barrymore. Niece of actress Diana Barrymore. Granddaughter of actor John Barrymore and Dolores Costello, on her father's side. Great-granddaughter of silent film actor Maurice Costello and Mae Costello. Great-niece of famed actors, Ethel Barrymore and Lionel Barrymore. |
| 71 | Chosen by People magazine as one of the 50 Most Beautiful People in the World. [1997] |
| 72 | Was engaged to Jamie Walters for a brief period of time. |
| 73 | Originally offered the lead role in Scream (1996) but chose to play Casey Becker because she thought this would be more fun. |
| 74 | Never finished high school. |
| 75 | She was, at seven years old, the youngest person ever to host. She was the Guest Host for Saturday Night Live (1975) when viewers voted that Andy Kaufman would never be allowed to return to the show. |
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