14. The Challenge
Release date: Nov. 25, 2003
Biggest supporting star: Theo Rossi, aka Juice from Sons of Anarchy, plays a competitor on Team Mayan with the twins.
Fashion takeaway: Carved charms on brown rope are the perfect bohemian necklace.
Why it’s No. 14: It’s no coincidence that Mary-Kate and Ashley Olsen’s last direct-to-video production The Challenge shares a name with what has become MTV’s long-standing reality series. The movie centers on vegetarian nature lover Shane (Mary-Kate) and her estranged type-A twin Lizzie (Ashley) who are cast on a Survivor-like reality show for ratings. Really, at this point in time, the last thing the world needed was more on-a-desert-island reality TV fare. And, of course, like with all Olsen twins movies, there are romance issues, but this one takes the cake. At the end of the movie, all of the twins’ on-screen boyfriends from previous movies show up and start arguing. Too much. No thank you. —JE
13. New York Minute
Release date: May 7, 2004
Biggest supporting star: Jared Padalecki, aka good boy-next-store Dean on Gilmore Girls, is the hot guy the girls crush on.
Fashion takeaway: Pink hair.
Why it’s No. 13: The wardrobe was really perfection. But that was about it. —EO
12. Getting There
Release date: June 11, 2002
Biggest supporting star: Shelley Malil, the 40-Year-Old Virgin actor who was sentenced to life in prison for attempted murder after stabbing his ex-girlfriend 23 times. He plays a Las Vegas Elvis impersonator named Raj who officiates weddings.
Fashion takeaway: Hats are necessary when you want to drive in a convertible.
Why it’s No. 12: Ten years after their first movie, things really started to take a dive with the Olsen twin films. I am 99% sure this was the first movie of theirs I owned on DVD and that worked out well because fast-forwarding went A LOT faster. Getting There — subtitled Sweet 16 and Licensed to Drive — followed Kylie (Mary-Kate) and Taylor (Ashley) as they drove with their friends in their new Ford Mustang to Salt Lake City for the 2002 Winter Olympics. By the time this movie came out, I was tired, they were tired, and it just fell flat. —JE
11. How The West Was Fun
Release date: Nov. 19, 1994
Biggest supporting star: Martin Mull, who is best known as Leon from Roseanne, plays Bart the jerk!
Fashion takeaway: Denim on denim.
Why it’s No. 11: When twins Susie (Mary-Kate) and Jessica (Ashley) accidentally get their father fired by trying to convince his boss he needs a vacation, they head with their clueless father to their granny’s ranch in hopes of reviving the struggling land and creating a new life there. But Susie and Jessica encounter more troubles when they meet Bart (a mean, mean man who retroactively haunted their dreams) and have to convince granny that Bart is trying to sabotage the ranch and sell it. The “kid(s) takes on the bad guy” plot line was done four years earlier and more cleverly by Home Alone. But the saving grace for this film was when the twins, in a moment of desperation, chose horseback as their means of transportation from the ranch to New York City. —EO
10. Switching Goals
Release date: Dec. 12, 1999
Biggest supporting star: A young Michael Cera!
Fashion takeaway: Bandana headbands.
Why it’s No. 10: Sam (Mary-Kate) is the tomboy sister, Emma (Ashley) is the girly sister (DUH!) When they’re picked for opposite soccer teams — one is terrible and one is coached by their father — they switch places so Emma can get better and Sam doesn’t have to worry about their father’s tough lessons. But of course, they get caught in the act and they both grow, on the field and in life, from the experience. Though this was a better portrayal of two very opposite twins than New York Minute, besides the whole “switching identities,” we know the twins are capable of — and great at — stirring up some trouble. —EO
9. When In Rome
Release date: Nov. 26, 2002
Biggest supporting star: No one, really. They were slacking.
Fashion takeaway: Jean jackets look FANTASTIC with florals.
Why it’s No. 9: I will not tell a lie: The 2010 movie of the same name starring Kristen Bell and Josh Duhamel is superior to this Olsen twins film from the end of their straight-to-video career. Besides the fact that they have perhaps their best movie names ever — Charli (Mary-Kate) and Leile (Ashley) — (and the added detail, of interest only to me, that there is a Jamie from New Jersey) this movie really has very little to offer. —JE
8. Winning London
Release date: March 27, 2001
Biggest supporting star: Jesse Spencer plays Lord James Browning Jr., another attractive boy that the sisters admire fondly.
Fashion takeaway: A trench coat completes any outfit.
Why it’s No. 8: Sisters Chloe (Mary-Kate) and Riley (Ashley) head to London to compete in a Model U.N. competition. But when the country they have prepared to discuss is selected by another team, they must scramble to learn everything they can about the United Kingdom (and the boys that live within its borders). The twins are always better together, and virtually shopping around London with these fashion icons didn’t suck either. —EO
7. Our Lips Are Sealed
Release date: Nov. 21, 2000
Biggest supporting star: Willie Garson, aka Stanford Blatch, as an FBI agent who is tasked with placing the twins and their family after they blow their Witness Protection Program identities over and over again.
Fashion takeaway: An Australian accent looks good on everybody. As do butterfly clips.
Why it’s No. 7: Twin sisters Maddie (Mary-Kate) and Abby (Ashley) Parker are placed in the FBI’s Witness Protection Program after they witness a diamond robbery at the local museum and end up helping send the thief responsible to jail, leading his uncle (the head of the Hatchew mob family of Yurugli) to come after them. Because they’re blabbermouths, they wind up blowing their cover and being sent all over the world and eventually, to Australia. What they don’t realize is that the thief stuck the diamond in their backpack and so the Hatchew (cue many a “bless you!” joke) family is still after them. Eventually, they stop him using a boomerang. Though this one gets extra points for location, it’s seriously lacking in the storyline department, and the absurdity level is super high. Ja’mie did it better. Also, I am now way too scared to ever eat Vegemite. —JE
6. Passport To Paris
Release date: Nov. 9, 1999
Biggest supporting star: Matt Winston is Jeremy, their stiff chaperone.
Fashion takeaway: Beaded necklaces. Beaded hair strands. Beads. Everywhere.
Why it’s No. 6: Melanie (Mary-Kate) and Allyson (Ashley) go to Paris to visit their grandfather. But he is too busy to spend time with them, so he puts them in the care of his assistant, Jeremy. Soon the sisters begin to live out every teenager’s fantasy. They ditch Jeremy, make friends with a fashion model, find two very attractive French boys and spend their afternoons running around Paris. What more does a movie need? —EO
5. Billboard Dad
Release date: Nov. 10, 1998
Biggest supporting star: Troian Bellisario as the girls’ diving teammate named Kristen.
Fashion takeaway: Tinted glasses with messy pigtail buns go with anything you’ve bought from PacSun.
Why it’s No. 5: In order to get their struggling artist and widower father (Tom Amandes of Everwood and now Parenthood) out of his slump, Tess (MK) and Emily (Ashley) miraculously climb up to a billboard and paint an ad seeking a girlfriend for him. (These girls never have a mom!) Not only do they find him a lovely lady — and put their negative feelings about her son behind them – but they also find a way to out their dad’s agent who’s selling knockoffs of his sculptures. Way to go, Tess and Emily! —JE
4. To Grandmother’s House We Go
Release date: Dec. 6, 1992
Biggest supporting star: Rhea Perlman, always one to play a villain, kidnaps the girls for ransom.
Fashion takeaway: Button-up shirts work at every age, for every occasion.
Why it’s No. 4: After overhearing their mom say how frustrated she was with them, sisters Julie (Ashley) and Sarah (Mary-Kate) decide to head to their grandmother’s house to give their single mother a break. But over the river and through the woods they end up taking the wrong bus, hopping on the back of a truck and being kidnapped. In one of their best, and most adorable, roles, nothing can deter these extremely wise beyond their years children. I’d be lying if I said as a child I didn’t think about the best ways to reenact this amazingly schemed plan.–EO
3. Holiday In The Sun
Release date: Nov. 20, 2001
Biggest supporting star: Megan Fox as bitchy department store heiress Brianna Wallace, who “get[s] what [she] want[s].”
Fashion takeaway: Your halter top and/or tube top should show a little bit of the bikini you’re wearing beneath it.
Why it’s No. 3: In this later-in-life film, Mary-Kate and Ashley play Madison and Alex Stewart, respectively, a couple of high-schoolers who fly on their dad’s private jet, complete with boxes of Krispy Kreme donuts and Fendi hats, to the Atlantis resort in the Bahamas begrudgingly because they wanted to go to Hawaii for winter break. Now, it makes me want to throw things. But 13 years ago, I couldn’t have worshipped the Stewart sisters more. There are water slide montages, dolphin riding, hang-gliding, and the girls even get sent to a Bahamian jail. Plus, I actually owned this soundtrack, which is fantastic: Little-known girl group Play performed their “hit” “Up Against The World” in crop tops and glittery jeans at an Atlantis party, Madison and Alex rode mopeds into town to “One Girl Revolution” by Superchick, and “Island in the Sun” plays in the opening credits. Wow, Weezer. Wow. The one downside to Holiday in the Sun? The movie ends like the series finale of The Hills, with the Olsens tearing back the curtain on the making of the movie. Too meta. This is not what I’m here for, ladies. –JE
2. Double, Double, Toil and Trouble
Release date: Oct. 30, 1993
Biggest supporting star: Cloris Leachman as the evil Aunt Agatha and saintly Aunt Sophia.
Fashion takeaway: A moonstone goes with everything.
Why it’s No. 2: I mean, Mary-Kate and Ashley’s second straight-to-video feature literally has everything, from racist pumpkin carving competitions to two Cloris Leachmans to Full House references to cookies as major clues in a horrifying mystery. Truly, it is the best. The only issue is that the twins — who play Lynn and Kelly Farmer — were still coming into their own and hadn’t quite reached their acting prime (or their on-point trending character name choices). Which is why there’s only one movie that can beat it… –JE
1. It Takes Two
Release date: Nov. 17, 1995
Biggest supporting star: Kristie Alley plays Diane, the PERFECT woman (and Amanda’s case worker).
Fashion takeaway: Grungy girly.
Why it’s No. 1: Not only is this the best Olsen movie of all time, it’s probably the best movie of all time. It’s the only film from the Olsen franchise that I still watch at least once a year. And yes, I cry every single time Alyssa (disguised as Amanda) is taken away from Diane at camp and put in the care of the worst parents ever. Amanda (Mary-Kate) and Alyssa (Ashley), identical strangers, ironically meet halfway between Alyssa’s summer house and Amanda’s foster care camp. The two decide to swap places in order to outsmart a gold-digging soon-to-be stepmom and a crazy foster family, put together the most romantic meetings for their respective father and case worker, AND start the best food fight of all time. And if that’s not enough, there really is no way to top a helicopter picking you up in a junkyard and landing in Central Park. –EO
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