Media Moments The Obama Sisters Can Never Erase

Sasha and Malia Obama have been in the spotlight since they were 7 and 10 years old, respectively, when their father, Barack Obama, was elected president of the United States in 2008. Whether they're getting flack for not being enthused about the annual Thanksgiving turkey pardoning or popping up on Snapchat during an intense game of beer pong, the Obama sisters have no doubt blossomed into young women with a presence of their own while under the public's watchful eye.

While their father's time as POTUS may have ended in January 2017, America's fascination with the Obama girls continues to this day. They've gone on to build adult lives on their own, forging budding careers, celebrity friendships, and even some romantic connections since their early days as the first daughters. While they may not be strolling the perfectly manicured lawns of the President's Palace any longer, the paparazzi still keep tabs as to what exactly these two are up to. 

Here are some of the top media moments from their time in and outside of the White House that Sasha and Malia Obama can never erase.

There's nothing like dear old dad getting the proverbial keys to the White House. At least, that's what Sasha Obama thought when she gave Barack Obama the ultimate sign of approval after he was sworn in as America's 44th president in January 2009. The former first daughter, who was just 7 at the time, adorably flashed her dad a thumbs up and a cheesy grin during the inauguration ceremony in a sweet moment captured by photographers. 

At the time, Sasha was the youngest child to call the White House home since John F. Kennedy Jr., who was only a couple months old when his father became president in 1961. She had a lot to grin about too, as visions of private chefs and a room fit for a queen awaited her and older sister Malia Obama. Not that the two didn't have their reservations about the big move. "They have a wonderful life in Chicago, they have lifelong friends in Chicago and the prospects of having to make new friends, that's never something that kids are looking forward to," Barack told People of his daughters in 2008, months before his win. "So I'm sure that there's a part of them that says we won't be heartbroken if things don't work out."

But who could forget that Sasha and Malia's father gifted them, as he'd promised following the campaign, a new puppy named Bo? Sasha may not have known it at the time, but she had a lot of reasons to give her stamp of approval. 

The Obama sisters have had their fair share of iconic moments, ones that some American citizens could only dream about. Malia and Sasha Obama had the privilege to meet with former South African President and Civil Rights leader Nelson Mandela in 2011 before he died just two years later. The daughters took a trip to South Africa to meet with the then-92-year-old peacemaker in his Johannesburg home, alongside their mother, Michelle Obama, and grandmother Marian Robinson. 

In a photograph shared by The Nelson Mandela Foundation (via the Times Union), Malia and Sasha are seen sitting on a sofa alongside Mandela and Michelle. The trip was part of a goodwill stop in South Africa and Botswana, marking a rare moment in which the retired anti-apartheid hero allowed visitors. Barack Obama paid a visit to South Africa alongside his daughters and Michelle two years later (pictured above), while Mandela was in the hospital at the time in critical condition. The family visited the former South African president's former prison cell, where he spent 18 out of 27 years fighting for the end of apartheid before his release. 

"Seeing them stand within the walls that once surrounded Nelson Mandela, I knew this was an experience they would never forget," the former president said of his daughters' visit to the prison, per The New York Times. Mandela died several months later at the age of 95. 

The annual presidential turkey pardon can admittedly be a corny ceremony. Throw in a few dad jokes, and you have a cringe-worthy time for any teenager, but both Sasha and Malia Obama were harshly criticized for seeming too disinterested at the event in 2014. According to the Independent Journal Review, GOP staffer Elizabeth Lauten called out both teens, telling them to "Dress like you deserve respect, not a spot at the bar" and "Certainly don't make faces during televised, public events." Lauten later apologized.

Keep in mind, Malia and Sasha endured holiday jokes from the commander in cheese for years: "I want to take a moment to recognize the brave turkeys who weren't so lucky, who didn't get to ride the gravy train to freedom," then-President Barack Obama quipped in 2016. Can anyone really blame them for rolling their eyes?

At what would have been their last turkey pardon that same year, the former first daughters were given a reprieve of their own and chose not to attend the ceremony. Barack's much younger nephews came out to see the turkey instead. "Thanksgiving is a family holiday as much as a national one, so for the past seven years, I've established another tradition: embarrassing my daughters with a corny-copia of dad jokes about turkeys," the then-POTUS quipped of the Obama sisters' absence (via ET). "This year, they had a scheduling conflict ... actually they just couldn't take my jokes anymore. They were fed up."

In a moment relatable to sisters everywhere (if sisters everywhere met celebs on the regular), Malia Obama played wing-woman for Sasha Obama when her little sis met actor Ryan Reynolds. The girls were dressed to the nines in ballgowns and attending their first state dinner in 2016, when White House photographer Pete Souza snapped an endearing image of the siblings meeting the "Deadpool" star. In the photo, Sasha looks giddy chatting with Reynolds while Malia photobombs her in the background with a thumbs up. Needless to say, social media lost its mind.

"Sasha Obama meeting Ryan Reynolds is all of us meeting Ryan Reynolds," one user tweeted (via Today) shortly after the photo was released. "I would literally die dead if Ryan Reynolds talked to me. You go, Sasha!!" another fan wrote. While there's no telling whether Malia was cheering her sister on or simply making fun of her total fangirl moment, the photo lives on in White House infamy.

Presidential teenagers are still teenagers. While their parents may be leaders of the free world, they are still adolescents who take the opportunity to snap a cute Instagram-worthy photo. The public was reminded of this oft-forgotten fact at the 2013 inauguration, when Malia and Sasha Obama whipped out their phones and started taking selfies during the inaugural parade. Given the fact that the all-day event required the girls to be at multiple engagements, could we really blame them for taking a quick selfie break?

Per BuzzFeed News, their duck faces and Sasha's froggy phone case nearly stole the show from their reelected father, who was busy being sworn in for a second term as the commander in chief. Sasha even tried to take a photo of her parents stealing a kiss, but Malia swooped in at the last minute to photobomb the moment. Talk about being comfortable in the spotlight!

Early in 2015, a grainy image emerged of a teenage girl fixing her long, dark hair and staring, lips parted, into the camera. The girl was (gasp!) Malia Obama in what the New York Post called "one of her first social media leaks since her father took office six years ago." In this day and age, that's an admirable feat for a teenager.

The Instagram pic was posted to Brooklyn rap collective Pro Era's account. In the since-deleted photo, Malia is sporting a white t-shirt with the band's logo. Coincidentally, the group is led by rapper Joey Bada$$, who was arrested and charged with assault while on tour in New Zealand around this time, as reported by Page Six. According to The Washington Post, a rep for Bada$$ said the photo was legit and had been received from a mutual friend of one of the group's members.

Until this image, we knew little about this first daughter's musical tastes — though who could forget when the Jonas Brothers surprised Malia and younger sis Sasha Obama as part of a scavenger hunt to get to know their way around the White House in 2009?

While on a college tour in 2015, Malia Obama decided to partake in (or at least observe) some traditional collegiate activities at Brown University. The Daily Caller (via Us Weekly) published a Snapchat screenshot of the then-first daughter standing close to a table littered with red plastic cups. X, formerly Twitter, exploded with observations from Brown students.

"Standing next to Malia Obama at a party nbd," read one of the many tweets (via BuzzFeed); another X user claimed the first daughter was "taking shots and playing beer pong." Brown students later apologized for the leaked photos through an editorial in the student newspaper, The Brown Daily Herald, admitting the campus "had no chill" during the visit. Needless to say, Malia chose to attend Harvard University instead.

But that wasn't the only college visit during which Malia was photographed near a beer pong game. In the summer of 2016, the Daily Mail obtained a photo of her — again via Snapchat — standing next to another table of cups and cans. She was allegedly at a house party in Maryland, and though an underage Malia wasn't actually seen holding or sipping a drink, the social media post went viral. Malia also reportedly attended a party in Martha's Vineyard during a family vacation. The former first daughter was rumored to have attended a wild party in 2016 in the area that was later broken up by police, but authorities could neither confirm nor deny her attendance as a matter of "national security," per the Boston Herald.

Fresh off her high school graduation, Malia Obama headed to Chicago to attend Lollapalooza in the summer of 2016. After the festival, Radar released a video that allegedly showed her smoking a cigarette that may or may not have contained marijuana. There were also photos and videos of Malia twerking at the concert.

While the footage made its rounds on X, some came to Malia's defense — including late Republican Senator John McCain's daughter, Meghan McCain, who reached across party lines to stick up for the then-first kid's party antics, tweeting to the tabloid Page Six to "leave Malia Obama alone!" Days after the incident, Malia was spotted wearing a "Smoking Kills" t-shirt — perhaps a tongue-in-cheek reference to the brouhaha?

Worth noting: Barack Obama admitted in his 1995 "Dreams from My Father" memoir that he smoked pot and "maybe a little blow" as a younger man (via The New York Times). Also, marijuana was decriminalized in Illinois, where Malia was allegedly caught with the alleged joint, allegedly.

During their time in the White House, the Obama ladies were known for their poise in public, but Malia Obama was moved to tears during a tender moment in Barack Obama's farewell speech in Chicago in January 2017. "Malia and Sasha, under the strangest of circumstances, you have become two amazing young women, smart and beautiful, but more importantly, kind and thoughtful and full of passion," their dad said, as Malia wiped her eyes. "You wore the burden of years in the spotlight so easily. Of all that I've done in my life, I'm most proud to be your dad."

Unfortunately, Sasha Obama was not able to hear her father's words in person, but not by any fault of her own. A White House official said little sis stayed home because "it was a school night and she [had] an exam in the morning," reported People.

It's no secret that Malia Obama is a big Lollapalooza fan. The former first daughter was spotted dancing to The Killers during the July 2017 show, writhing around on the ground, and generally having more fun than the rest of us. Sources told TMZ that she spent most of her time backstage with a pal, but that she came out to dance in the general area with plebeians a few times.

But Malia may have had a little too much fun at Lollapalooza, given the aftermath. TMZ spied her being driven around in a golf cart, seemingly out of it. You can see her seeming to nod off in the video, though it's a bit unfair to assume anything shady was the cause — after dancing around outdoors in heat and sun all day, exhaustion and dehydration are possible, and considering she's the daughter of a former president, chances are security (including transportation) would have been provided no matter what condition she appeared to be in.

She did have a legit mishap, however. Page Six reported that she lost her phone at the music festival. "Malia came into the Apple Store to get her iPhone replaced, but things didn't go exactly [as planned]," a source said. "The Apple Store couldn't immediately help her because she didn't have the Apple ID or the password for the missing phone, since the White House set it up."

From the White House to nightclubs — Malia and Sasha Obama have had quite the transformation. According to Page Six, the sisters were seen partying the night away at an exclusive party for Drake in August 2023 at the Bird Streets Club in Los Angeles. The former first daughters made headlines when they ditched their casual California attire for midriff-baring skin-tight looks to celebrate the rapper's after-party following his concert with 21 Savage. Malia was seen wearing a tight long-sleeve lace-up top matched with semi-sheer pants, while Sasha rocked a black lace corset bra with baggy cargo pants.

Malia and Sasha, who live together in their Los Angeles home, were seen leaving the event around 4 a.m. The University of Southern California graduate led the way to the car as Malia trailed behind, shielding her face from the paparazzi snaps. The two share their love for Champagne Papi with their father, who has previously endorsed Drake's desire to star as former President Barack Obama in a potential biopic about his life. 

"I will say this, Drake seems to be able to do anything he wants. I mean, that is a talented, talented brother," Barack admitted on Complex's "360 With Speedy Morman" in 2020, before trailing off with, "So, if the time comes, and he's ready..." He went on to add, "Drake has — more importantly, I think — my household's stamp of approval. I suspect Malia and Sasha would be just fine with it."

Habits are hard to break, and Malia and Sasha Obama just might be learning that the hard way. The sisters have both been photographed smoking cigarettes out and about in Los Angeles, where they both live full-time after graduating college. With Sasha ending her final semester at the University of Southern California in May 2023, and Malia embarking on new endeavors in her burgeoning showbiz career, the two may be blowing off some much-needed steam. 

Paparazzi caught Malia taking drags from a cigarette as she talked to a friend outside of a convenience store that October, years after photos of her smoking a joint at Lollapalooza sent social media into a spiral. A month earlier, Sasha was seen puffing on a cigarette with friends in West Hollywood, something the USC graduate hadn't been seen doing before (at least, not in the prying eyes of the paparazzi). 

The former first daughters may have been taking after their dad, once an avid smoker himself. In Barack Obama's 2020 memoir "A Promised Land" (via CNN), he admitted he would sometimes smoke up to 10 cigarettes daily to cope with the stress of being president. "As a former smoker, I constantly struggle with it. Have I fallen off the wagon sometimes? Yes. Am I a daily smoker, a constant smoker? No," he said during a 2009 press conference, per Reuters. "I don't do it in front of my kids, I don't do it in front of my family. I would say that I am 95% cured, but there are times where I mess up."

Malia Obama is all grown up — and from the looks of it, she may have a new mystery man in her life! At least, at the time of this writing. The former first daughter was rumored to have dated record producer Dawit Eklund beginning in the summer of 2022, but their relationship was never confirmed. The Harvard University graduate made headlines again in September 2023, when photos published by Daily Mail featured her on what appeared to be a sushi dinner date in Los Angeles with rapper Anime. Malia was later seen walking arm-in-arm with the musician. 

But it seems Malia may be keeping her options open, as paparazzi also caught her getting close to an unnamed man behind a tree just a few days before her meal with Anime. There's no clear sign that the two were getting in a quick smooch or simply hugging each other, but the duo later departed separately in their respective cars after enjoying lunch during a shopping trip together, per Hollywood Life. She was seen chatting with another mystery dude in Hollywood that November during a night out on the town.

Of course, this wasn't the first time people took note of Malia's super-private relationship history, as her low-key romance with college beau Rory Farquharson also made headlines. "I think it's wonderful," Michelle Obama told "Good Morning America" in 2022 of her daughters' dating lives. "I want them to know what they want and who they are in a relationship. And that takes trying on some people."