Which Year Was This Celebrity Photo Taken?


“The camera,” the late art historian John Berger once said, “relieves us of the burden of memory.” But what photographers no longer have to remember can become vitally important to those of us who weren’t present when the photograph was taken; it becomes a crystallized moment in time, a way of getting behind the bodyguards and velvet ropes that separate the lives of celebrities from our own. Photographs and video are the only way most of us can see celebrities and witness their most iconic moments.

These four decades of celebrity photographs capture some important milestones in pop culture history, but there was a time not that long ago when these events were happening in specific places, in front of specific people, and not available for the rest of us to see. The image in a photograph seems eternal, disconnected from time, but the moment it captures is a fleeting one like any other. For us, these photographs represent the past; for the people in them, they used to be the present.

We’ve selected 25 photographs from semi-recent pop culture history, and told you a little bit about the context of each. Armed with the image, and a little background information, can you connect the eternal with the transitory? Can you name the year?

Question 1

Fight Club

Sylvester Stallone’s passion project, Rocky, had just made him a household name. But Muhammad Ali had been a household name for a very long time, and this wasn’t about to change—he still had another title win ahead of him at the time this photo was taken. Cinema’s greatest boxer and reality’s greatest boxer collided, sort of, when Ali (his tongue firmly planted in his cheek) crept up on Stallone at the Academy Awards. But which year’s Academy Awards were they?

Question 2

Rhapsody in Blue Denim

Did any celebrity power couple sum up 1990s kitsch better than Britney Spears and Justin Timberlake? Britney was by far the bigger solo star at this point, but Justin, widely regarded as the hottest member of N’Sync, would soon resolve his questionable facial hair situation and become a pretty big deal in his own right. (He actually appears twice in this quiz.) We’ve grown to love Britney and Justin so much that it’s easy to forget how creepy the tabloid press made their relationship seem at the time. If they weren’t intentionally trolling the paparazzi with these matching denim outfits, they certainly could have been. Name the year.

Question 3

Rihanna at Harvard

Rihanna at Harvard

Robyn Rihanna Fenty may be one of the biggest-charting figures in pop these days, but she hasn't forgotten her roots. "I don't want to get lost in this big cushion of success," she told The New York Times in 2015. For her work promoting international children's healthcare and contributing to public health and economic development in her home country, the Barbadian-American singer-songwriter and founder of the BELIEVE Foundation was declared Harvard University's Humanitarian of the Year. But in which year, exactly?

Question 4

Let Me Tell You Something, Brother

Andre the Giant was by all accounts one of the nicest people to ever lace up boots, but the big guy—who had been a fan favorite for over 20 years—voluntarily took on the role of villain to help catapult a rising young star named Hulk Hogan to the top of the World Wrestling Federation, now known as World Wrestling Entertainment (the WWE). In the main event of WrestleMania III, Hogan bodyslammed Andre in front of over 93,000 spectators at the Pontiac Silverdome. Name the year.

Question 5

Some Late Night Jazz

Running for president looks like a lot of things, but “fun” isn’t generally on the list. All that changed when Bill Clinton appeared on The Arsenio Hall Show with a saxophone and played the melody to Elvis Presley’s “Heartbreak Hotel.” That may not sound so impressive now, but imagine how stiff things were a generation ago in order for this to have been a major, groundbreaking event. Since then, things have loosened up; we’ve seen George W. Bush circle dance with the Kankouran West African Dance Company and Barack Obama belt out a verse of “Sweet Home Chicago.” But in the year he did it, Clinton’s saxophone appearance really did turn heads. Which year? You tell us.

Question 6

Yeezus Interruptus

Half the fun of the MTV Video Music Awards is that you never know what’s going to happen next. When Madonna writhed on the floor in a wedding dress to perform “Like a Virgin” at the first VMAs in 1984, it was pretty unusual for Madonna—but it would turn out to be pretty par for the course for the VMAs as a whole. But one moment got a little serious: when Taylor Swift won Female Video of the Year over Beyoncé, it shocked observers. This was, after all, the year Beyoncé released “Single Ladies (Put a Ring on It).” Frustrated by the decision, Beyoncé’s friend and occasional collaborator Kanye West, stepped on stage, took the mic, and publicly called for Beyoncé to get more award recognition. Later that night she did, winning Video of the Year. Which year was it?

Question 7

Yep, She's Gay

People who don’t remember the 1990s may look at the cover above and wonder what the big deal was, but there was a time not very long ago when it was unheard of to see an openly lesbian or gay comedian with their own sitcom. Ellen DeGeneres, star of ABC’s Ellen, took a huge gamble when both she and her character came out. Although her sitcom was not renewed the following year, Ellen went on to find success as the voice of Dory in Finding Nemo and, more recognizably, as the host of ABC’s long-running daytime staple The Ellen DeGeneres Show. But the real measure of her success is the number of openly lesbian and gay performers who can now work in television without keeping their personal lives under wraps. In 2016, she received the Presidential Medal of Freedom for her courage. When did she come out?

Question 8

The Power Couple

The Beirut-born British international human rights attorney Amal Alamuddin was already a pretty big deal long before she met the American actor George Clooney, but professional recognition for your achievements is one thing; being married to ER’s former “Hot Doc” is another. All things considered, the tabloids were probably a lot less hard on her than most observers would have predicted—even if they didn’t always do a great job of acknowledging that her achievements had been at least as impressive as his. This photo was taken the year they got married. Which year was that?

Question 9

Nerd Culture Goes Mainstream

There was a time when being a big fan of George R.R. Martin’s series A Song of Ice and Fire marked you as a fantasy nerd who loved long, sprawling, multi-book epics. When it was adapted for HBO under the title of its first book, A Game of Thrones (originally published in 1996), it gave the dark swords-and-sorcery series more of a mainstream audience than it had ever had before. When this photo was taken at San Diego Comic Con the year the TV series debuted, the cast and creator were socializing in their element: among fantasy nerds who understood fantasy nerd culture. Name the year.

Question 10

The Daily Show Grows Up

When Jon Stewart took over The Daily Show from Craig Kilborn in 1998, he inherited a fairly light, fluffy comedy news program in the grand tradition of SNL’s Weekend Update or HBO’s Not Necessarily the News. In the two decades since then, under Stewart and his own successor Trevor Noah, it has become something much more important: a source of real analysis and commentary, not just humor, and an essential destination for national politicians interested in connecting with cynical, media-savvy young voters. One of the events that helped make The Daily Show what it is was the series’ first interview with Barack Obama. When did that happen?

Question 11

The Kid is Not My Son

If you grew up watching Michael Jackson, well, grow up, you probably still remember the wholesome, sweet-faced kid who played the Scarecrow in The Wiz and once sang a love song about a pet rat. But “wholesome” and “sweet-faced” does not describe the image of many successful adult male performers in the cutthroat music video era of the 1980s, and Michael knew it. He had to reinvent himself. On Motown’s 25th anniversary special, he did just that—performing his sexually charged hit “Billie Jean” wearing a suit, a single sequined glove, and a perpetual snarl. Nobody who saw the special ever looked at him the same way again. Name the year.

Question 12

The Dress

The Theiss Titillation Theory, attributed to Star Trek fashion consultant William Ware Theiss, states that “the sexiness of an outfit is directly proportional to the possibility that a vital piece of it might fall off.” Jennifer Lopez’s green chiffon Grammy dress, designed by Donatella Versace and generally referred to afterwards as simply “the dress,” seemed to illustrate this principle as few other dresses had, boosting Donatella’s cred in the fashion industry and giving J-Lo more publicity than she’d ever had before. Despite appearances, the dress itself—secured with an impressive amount of double-sided fashion tape—was at least as likely to hold together as anybody else’s. But the audience reacted just as Theiss would have predicted; co-presenter David Duchovny of The X-Files remarked that night that “this is the first time in five or six years that I’m sure nobody is looking at me.” Name the year.

Question 13

Who Speaks for Earth?

A brutally honest thirteen-hour public television series about the structure of the universe and the future of humanity wouldn’t be most people’s idea of a blockbuster, but the late Carl Sagan’s contagious enthusiasm for science, his undeniable fashion sense (black turtlenecks would never be the same), and his soothing, pastoral voice shone through and made scientists out of us all. Although we ultimately lost Sagan to myelodysplasia-related pneumonia in 1996, an updated version of the series, produced by Family Guy’s Seth McFarlane and hosted by astrophysicist Neil deGrasse Tyson, captivated a new generation of viewers in 2014. But what year did the original series air?

Question 14

Dangerously in Love

It is becoming difficult to remember that at one point, there was such a thing as contemporary pop without Beyoncé. After achieving near-unprecedented levels of success as the perceived lead performer of Destiny’s Child, Beyoncé Knowles achieved entirely unprecedented success as a solo performer. Her debut album Dangerously in Love did for the twenty-oughts what Michael Jackson’s Thriller and Madonna’s True Blue did for the eighties. This photo, taken at the Golden Globes the year of her solo debut, captures her transition from team player to global phenomenon. Name the year.

Question 15

Bill the Conqueror

Before “the cloud” and “Web 2.0,” before “the information superhighway” and “the bridge to the 21st century,” there was Bill Gates. With an 88.9 billion dollar net worth, Bill is still the wealthiest person on Earth—and through the Bill and Melinda Gates Foundation, he’s been using his wealth to fight global poverty, hunger, and disease. But when this picture was taken, during the promotional tour for the first Windows mass release, he was just a nerdy kid with a dream. Name the year.

Question 16

Letting the Right One Out

The often-Googled term “wardrobe malfunction” was first used after the infamous Super Bowl XXXVIII halftime show, during which the right breastplate of Janet Jackson’s outfit came loose and revealed her nipple jewelry for 9/16th of a second. Although the possibility of fleeting accidental nudity had been part and parcel of live television for decades (and was even arguably one of its selling points), the resulting $550,000 fine from the FCC (later overturned by the U.S. Supreme Court)—the end result of a massive nationwide complaint campaign organized by a pro-censorship group—sent a chilling message to live broadcasters. Name the year.

Question 17

The Royal Treatment

In the wake of Princess Diana’s tragic death, it’s hard to remember that there was a time when she and her new husband, Prince Charles, represented hope for the future of British royal tradition. Charles and Diana represented Britain’s own original Camelot—a glamorous young couple in the mold of the Kennedys—and their wedding was a global event, at least in countries that belonged to, and/or still had some affinity for, the British Commonwealth. In the end, it’s estimated that over 750 million people saw Charles and Diana exchange their vows. Name the year.

Question 18

She Put a Spell on You

The biggest literary event of the 21st century so far has been the release of J.K. Rowling’s seven-book Harry Potter series. And Rowling’s own story, as a working-class aspiring writer who climbed her way up to billionaire status and then intentionally donated enough money to make herself a non-billionaire again, is almost as impressive as Harry’s. When Rowling published the last volume of the series, the 759-page and ominously-titled Harry Potter and the Deathly Hallows, it was the culmination the artistic self-discipline that had come to define her career. She could have kept the series going forever, just as she could have let her wealth accumulate forever, but Rowling knows what most of us don’t: she knows when to let something end. Name the year.

Question 19

The Kessel Run in 20 Parsecs

If you grew up watching the Star Wars movies, you spend blow hours happily going through old photos and just watching how much fun the cast had making and promoting the films. Harrison Ford, Carrie Fisher, and Mark Hamill had as much chemistry off screen as on, and it shows. It’s not clear what they’re talking about here at the original Empire Strikes Back premiere, and it isn’t really any of our business, but you can see a hint of the offscreen dynamic that made the films so re-watchable. Name the year.

Question 20

We Need to Talk

There were talk show hosts before Oprah Winfrey, and there were talk show hosts after Oprah Winfrey, but there were no talk show hosts like Oprah Winfrey. Rather than presenting her guests as spectacles to gawk at, she sat down and interacted with them as human beings. Instead of telling her viewers to stay tuned, she set up a viewers’ book club and encouraged us to read. She used daytime television to appeal to the best parts of us, and the fact that this succeeded reflects as well on American viewers as it does on her. Here’s a photo from her first episode. Name the year.

Question 21

Simply the Best

The diversity of the Academy Awards (or lack thereof) has been a hot topic for years, spawning an often bitingly clever #oscarssowhite hashtag meme and an Academy membership that has gradually become slightly more diverse. But there was only one moment like the 74th Academy Awards, when African-American stars claimed both of the top acting categories—Halle Berry for Best Actress (for Monster’s Ball), Denzel Washington for Best Actor (for Training Day). At the same event, Sidney Poitier, the only black actor before that point to have won a lead best-acting Oscar (for The Lilies of the Field in 1963), won a lifetime achievement award. Name the year this photo was taken.

Question 22

The Gaulthier Effect

There have been many trendsetting performers over the past several decades, but have any of them set more trends than Madonna? The trendiest of all, the so-called “cone bra,” wasn’t originally a bra at all; it was a corset, designed by Jean-Paul Gaulthier, that Madonna wore during her Blond Ambition tour. Gaulthier had originally designed the cone-bra corset when he was a child as a costume for his beloved teddy bear, Nana. This photo from the tour shows off Madonna’s Blond Ambition look: muscular, provocative, and uncharacteristically severe. Name the year.

Question 23

What's Love But a Secondhand Emotion?

No figures influenced 1970s rock, funk, and everything besides more than Ike and Tina Turner. When Tina revealed the extent of Ike’s physical abuse in her autobiography I, Tina (1986), it was a reminder of the horrors that can lie bubbling under the surface of the art we consume. In the adaptation What’s Love Got to Do with It?, Angela Bassett portrayed Tina Turner with her blessing, while Tina recorded the soundtrack. This photo was released during the film’s promotional tour. Name the year.

Question 24

It's Always Someone Else I See

Elton John’s “Don’t Let the Sun Go Down on Me” did pretty well as a radio single in 1974, well enough that a young singer named George Michael remembered it fondly and started regularly covering it at his own sold-out concerts. At one of these concerts, Elton John surprised the audience by coming on stage to make a duet out of it—and this version of the song, released as a single, became the definitive version, topping the charts and changing the careers of both men. Name the year.

Question 25

The Last Ride

The Harlem-born Tupac Shakur, son of Black Panther activists Mutulu and Afeni Shakur and godson of fugitive activist Assata Shakur, blended nineties rap’s invincible braggadocio with a level of sophistication and social conscience that few artists in any genre could match. He was gunned down on the way home from a Mike Tyson boxing match at the ludicrously young age of 25, but the 21 posthumous albums bearing his name are a testament to his productivity and his legacy. This photo was taken minutes before the shooting. Name the year.

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