How many of these hit ’90s movies can you guess from a single image?
Remember how many you get right…
…because we’ll tell you how you scored at the end.
Let’s start with…
1990
Recognize the mysterious blonde woman in the image above?
This is a very easy one if you’re a fan of ’90 movies. This film was discussed quite a lot then, and still has millions of diehard fans today.
Ready? It’s…
1990 Answer: Pretty Woman
Pretty Woman, the No. 4 movie at the worldwide box office in 1990, stars Julia Roberts as Vivian (seen above sans wig and after an expensive Beverly Hills makeover) and Richard Gere s Edward, a wealthy businessman who hires her for what he expects to be a short-term engagment.
This is one of the happiest movies about sex work: It plays out like a fairy tale, thanks to the incredible chemistry between Roberts and Gere, who, a decade earlier, played a male sex worker in American Gigolo.
Julia Roberts was already on the rise before Pretty Woman, but the film started her reign as the undisputed queen of ’90s rom-coms.
1991
That’s obviously Sean Connery, above.
But what period ’90s movie featured him going medieval?
Ready? The answer is…
1991 Answer: Robin Hood: Prince of Thieves
If you didn’t see Robin Hood: Prince of Thieves, you may not know Connery’s even in it. His cameo as King Richard was a delightful surprise for Robin Hood fans, especially those who remembered his turn as Robin Hood in the 1976 romantic adventure Robin and Marian.
He’s one of many reasons to see Robin Hood: Prince of Thieves, which also features Costner in the title role, Morgan Freeman as Azeem and a scene-stealing Alan Rickman as the Sheriff of Nottingham.
The film was the No. 3 movie at the worldwide box office in 1991, continuing Kevin Costner’s phenomenal box office run.
And now, onto the next film on our list…
1992
Surely you can recognize the queen of the night in the picture above.
But what film could the publicity image be from? Perhaps a forgotten sci-fi epic?
No. It’s…
1992 Answer: The Bodyguard
Whitney Houston starred opposite Kevin Costner, one of those movies with something for everyone: It has drama, action, romance, and an absolutely incredible soundtrack, including Houston’s show-stopping cover of Dolly Parton’s “I Will Always Love You.”
It was the No. 7 film at the worldwide box office in 1992.
The film was directed by Mick Jackson, and written by Lawrence Kasdan, who produced it with Jim Wilson and Costner — who was truly enjoying a level of acclaim and box-office success rarely matched in Hollywood history.
Ready for 1993?
1993
The excellent actor on the right wore a lot of disguises in the very cool thriller seen above.
It’s another movie with everything… well, except a killer Dolly Parton cover.
But it does have thrills, chills, action, slow-burn romance, endless charm, and perfect performances.
Ready? It’s…
1993 Answer: In the Line of Fire
Clint Eastwood was fresh off winning Best Picture and Best Director for 1992’s Western Unforgiven when he starred in In the Line of Fire, letting Wolfgang Peterson handle director duties.
Eastwood plays Frank Horrigan, who was one of the Secret Service agents on the day John F. Kennedy was assassinated. He starts receiving taunting phone calls from John Malkovitch’s “Booth,” who is plotting to kill the current president — unless Corrigan can outsmart him.
This is the definition of a crackerjack thriller, and Eastwood is at his most appealing as a capable old hand happy to smile along with all the jokes about his age: It turns out being underestimated is a huge advantage in his line of work.
In the Line of Fire was the No. 7 movie at the worldwide box office in 1992. (By the way, all of these numbers come from BoxOfficeMojo.)
1994
If you saw the adult versions of these characters, you would recognize them immediately.
But these young actors — the terrific Michael Conner Humphreys and Hanna Hall — are playing them in their younger years.
If you have a guess what film they’re in, run to the next entry.
1994 Answer: Forrest Gump
Robin Wright and Tom Hanks played the adult versions of Jenny and Forrest in Forrest Gump, a simply beautiful movie by Robert Zemeckis that won six Oscars, including Best Picture, Best Director for Zemeckis, and Best Actor for Hanks.
It was also a hit with audiences, becoming the No. 2 movie at the 1994 box office. If we ever make a list of movies that have made us cry, this will be on it. (The part where he meets his son; thanks for asking.)
Zemeckis, Wright and Hanks recently reunited for 2024’s Here, written by Forrest Gump screenwriter Eric Roth.
It’s wild to us that the movie Forrest Gump is now further in the past than the Vietnam War was in the movie Forrest Gump.
And now, let’s speed ahead to the next year…
1995
Drew Barrymore, a beloved child star in the ’80s, stepped into grown-up roles in the 1990s, including in the blockbuster above.
We wish she’d had a bigger role in the movie, which was absolutely packed with established and rising stars, including the biggest comedy actor of the decade.
Ready? It’s…
1995 Answer: Batman Forever
Along with the great Debi Mazur, Barrymore played one of two molls of the villainous Harvey Dent, aka Two Face, played by Tommy Lee Jones.
She’s seen above with Jim Carrey, who played The Riddler.
Val Kilmer, meanwhile, donned the Batsuit for this one, which continued the Batman saga that started with Tim Burton’s 1989 Batman. Joel Schumacher, taking over as director, decided to run with Burton’s campy elements and see how far he could go.
The result was the No. 4 worldwide hit of 1995.
And now, time for the next image…
1996
You probably recognize the two handsome gents in the image above. Both are still very much in demand.
But do you remember the thriller that paired them up?
We’ll give you some time to think.
OK, ready? Let’s go…
1996 Answer: A Time to Kill
Matthew McConnaughey had his breakout role in this John Grisham adaptation, playing the defense lawyer of Samuel L. Jackson’s Carl Lee Hailey.
Carl Lee goes after two white men who brutally attack his daughter, and McConnaughey’s Jake Brigance makes the case that Carl Lee was justified.
This is the second consecutive film on this list to be directed by Joel Schumacher. It was the No. 10 movie at the worldwide box office.
Ready for 1997?
1997
Who’s the prim and proper lady above?
It’s clearly a period film, right? Can you remember which one?
Hm, maybe some dry Merchant Ivory production?
No. It’s…
1997 Answer: Titanic
Frances Fisher played Ruth DeWitt Bukater, mother of Kate Winslet’s Rose, who urges her to marry the insufferable (but very rich) Cal, played by Billy Zane.
Instead, she chooses — for a tragically short time — the poor but lovable Jack Dawson (Leonardo DiCaprio.)
Together, they power one of the greatest love stories of all time. Titanic, written and directed by James Cameron, was easily the biggest hit of the ’90s, and was, for a while, the biggest hit ever. It was displaced from the top in 2009 by another Cameron film, Avatar.
1998
Recognize the nice young couple above?
As threatening as rice can be, they — and everyone on earth — are about to face an even bigger threat.
Name the movie, if you can.
Ready? It’s…
1998 Answer: Armageddon
The Michael Bay action thriller boated a stellar cast that includes not just Ben Affleck and Liv Tyler, but also Bruce Willis, Billy Bob Thornton, Steve Buscemi, Michael Clarke Duncan, Owen Wilson, and many more.
It was the biggest worldwide hit of the year.
And Tyler’s dad, Steven Tyler, sang the theme song, “I Don’t Want to Miss a Thing” with Aerosmith. That’s synergy.
1999
If you saw the film above, you’ll get this one immediately.
If you didn’t, you should see it. But not alone, and not before going camping.
OK? Ready? It’s…
1999 Answer: The Blair Witch Project
Main image: The Blair Witch Project. Artisan Entertainment
The Blair Witch project is one of the most notable movies of the ’90s in many ways: It’s one of the scariest movies ever made, it helped launch the found-footage horror subgenre that’s still going strong today, and it’s one of the most profitable movies of all time.
Directed by Daniel Myrick and Eduardo Sánchez, and starring Heather Donahue, Michael C. Williams, and Joshua Leonard as documentarians who go looking for a witch, it drew and haunted audiences who weren’t totally sure, in the early days of the internet, how much of it they should believe.
It was the No. 11 biggest hit worldwide in 1999, closing out the ’90s with a grungy, DIY aesthetic no one has matched since.
How Did You Score on Guessing These Hit 1990s Movies From a Single Image?
9 or more correct.. Nirvana
7 or more correct… Secret Service
5 or more correct… Happy Gilmore
3 or more correct… Steerage
Fewer than 3 correct… I award you no points, and may God have mercy on your soul.
Also, all of the ’90s movies on this list are now available on disc and digital. We recommend seeing them all.
And if you love ’90s movies, you may also enjoy testing your knowledge of ’80s movies.
Main image: The Blair Witch Project. Artisan Entertainment
