Some of our favorite stars started out by appearing in classics from the 90s, 80s, and even earlier! From raunchy romcoms to thought-provoking dramas, America clearly appreciates a love story, and many of the genre’s greatest hits have featured stars that have become American favorites. Join us as we see where some of Hollywood’s favorite pairings are today. You never know. Some of your favorites may even appear on this elite list more than once.
Olivia Newton-John And John Travolta: Then
Olivia Newton John And John Travolta Then
The classic musical Grease is the 29th highest-grossing film in the history of cinema and breaks into the top ten for highest-grossing PG films of all time. What makes this even more impressive is the fact that the film had a very small budget of just $6 million today. John Travolta and Olivia Newton-John were the main attractions of the film, and it went on to make almost half a billion dollars in theatres worldwide.
Olivia Newton-John: Now
A familiar face for more than 40 years, Olivia Newton-John has credits dating back to 1973. And she hasn’t slowed down since playing Sandy in “Grease. ”Olivia Newton-John has graced screens, big and small, for more than four decades now. She got her start all the way back in 1973. Since playing the young Sandy in Grease, she certainly hasn’t slowed down. Most recently, she starred alongside Maya Rudolph and Amy Poehler in the Netflix film “Wine Country. ” She has an estimated net worth of $40 million, plus 136 soundtrack credits to her name. An actress and songstress! Very impressive indeed.
Olivia Newton John Now
John Travolta: Now
It’s no exaggeration to say that John Travolta is one of the most prolific actors in Hollywood. In fact, he has over 70 acting credits to his name. The actor has seen success on the big and small screens. When his career slowed down in the late 80s, many thought it was over, but it got a boost when he featured in Quentin Tarantino’s smash hit “Pulp Fiction.” His net worth is over $170 million.
John Travolta Now
Barbra Streisand And Robert Redford: Then
Back in 1973, viewers got the chance to see Barbra Streisand and Robert Redford together on screen in “The Way We Were.” The film went on to make $45 million at the American box office and tells the story of a couple ripped apart by incompatible political views. The film earned two Oscars at the Academy Awards but was nominated for a further four more. It’s well regarded as a classic in American dramatic cinema.
Barbra Streisand And Robert Redford Then
Barbra Streisand: Now
Barbra Streisand has an impressive net worth of $400 million, plus a brilliant 86 soundtrack credits that date back to the mid-20th century. She starred in just 23 films, but these include “Meet the Fockers” and “The Prince of Tide.” When adjusted for current inflation, her film library has generated more than $2.7 billion at the American box office. For her role in “The Way We Were,” she was nominated for an Academy Award.
Barbra Streisand Now
Robert Redford: Now
Robert Redford is one of the wealthiest senior celebrities in Hollywood, being over 70 now. He’s been in the business for about as long too. His credits date all the way back to the 60s and include roles in “The Natural,” “Spy Game,” “Butch Cassidy and the Sundance Kid,” “Out of Africa,” and “All the President’s Men. ” Most recently, he starred as a villain in “Avengers: Endgame,” and has a net worth of $170 million.
Robert Redford Now
Meg Ryan And Billy Crystal: Then
One of history’s greatest romantic comedies is undoubtedly the 1989 hit, “When Harry Met Sally….” It starred Meg Ryan and Billy Crystal and was nominated for an Oscar and five Golden Globes. The film followed a classic “will they, won’t they” set up and overtime has grossed over $92 million at the American box office. The film is enjoyed by thousands to this day, and scenes are often referenced in much of American pop culture.
Meg Ryan And Billy Crystal Then
Meg Ryan: Now
Meg Ryan has a respectable net worth of over $45 million, and it’s all thanks to nearly 50 acting credits, which date back all the way to 1981. She’s a romantic comedy staple, having also starred in “Sleepless in Seattle,” and the younger “You’ve Got Mail.” She’s also starred in “Top Gun,” “Courage Under Fire” and “When a Man Loves a Woman.” All totaled, her films have grossed over $2 billion at the box office.
Meg Ryan Now
Billy Crystal: Now
Since the mid-70s, Billy Crystal has been a serious Hollywood favorite. His filmography includes such films as “Running Scared,” “Throw Momma From the Trains,” “City Slickers,” and “The Princess Bride.” His films have grossed over $2 billion, he’s received three Golden Globe nominations, and his net worth sits at a respectable $45 million. One of his most recent films is the well-received “Standing Up, Falling Down.” He’s also made regular appearances on Saturday Night Live.
Billy Crystal Now
Julia Roberts And Richard Gere: Then
“Pretty Woman,” which stars Richard Gere as a businessman, and Julia Roberts as a woman of the night, is one of the most loved and most successful romantic comedies of all time. The film had a budget that’s slim by today’s standards, at just $14 million, but it went on to earn half a billion dollars globally. It is also the fourth highest-earning romcom of all time. The film was nominated for one Academy Award.
Julia Roberts And Richard Gere Then
Julia Roberts: Now
Julia Roberts hardly needs an introduction. She has a net worth o $200 million, making her one of the richest actresses of all time. She has over 60 acting credits to her name. Her most well-known film is perhaps “Erin Brockovich,” but most recently, she has begun starring in the Amazon Prime series “Homecoming.” Her filmography has earned over $6 billion at the global box office. Unsurprisingly, “Pretty Woman” leads this prestigious pack of films.
Julia Roberts Now
Richard Gere: Now
Richard Gere is a distinguished actor, and “Pretty Woman” is also his biggest film of all time. That’s quite an interesting fact when you consider that he’s starred in nine films that each made over $100 million worldwide. His career dates back to the early 1970s and contains such hits as “Runaway Bride,”, Internal Affairs,” “Primal Fear,” “The Jackal,” “Chicago,” and “Haichi: A Dog’s Tale.” His net worth is a tidy $120 million in total.
Richard Gere Now
Mary Stuart Masterson And Eric Stoltz: Then
In the film “Some Kind Of Wonderful,” Eric Stoltz’s character obsesses over his dream girl, only to miss the fact that his tomboy best friend, played by Mary Stuart Masterson, is actually the right one for him. It was released in 1987 and earned a great $18.55 million at the American box office. It was produced by the prolific John Hughes, whose film library has made roughly $800 million at the worldwide box office.
Mary Stuart Masterson And Eric Stoltz Then
Mary Stuart Masterson: Now
Mary Stuart Masterson made her debut in “The Stepford Wives” in 75, while she was still just a young child. Since that role, she’s racked up over 50 credits on film and in TV shows. Most recently, she starred in “Blindspot” but has also appeared in long-running shows such as “Blue Bloods,” “The Good Wife,” “NCIS,” “For Life,” and “Law & Order: SVU.” Her current net worth is estimated to be a humble three million dollars.
Mary Stuart Masterson Now
Eric Stoltz: Now
Eric Stoltz has a long and busy acting career. Here’s a fun fact: He was originally meant to play Marty McFly in Back to the Future, but the director felt he was a little too serious for the role. He’s also starred in “Pulp Ficition,” and as a child, he starred in the drama “Mask.” For his portrayal of Rocky Dennis in that film, he was nominated for a Golden Globe. An impressive child star.
Eric Stoltz Now
Cameron Diaz And Ben Stiller: Then
Outrageous for its time, “There’s Something About Mary” still holds up today and follows Ben Stiller’s character trying to salvage a relationship with his high school crush after a terrible date. The movie won four MTV Movie Awards and was nominated for two Golden Globes. It follows “Pretty Woman” as the fifth highest-earning romantic comedy, as it earned just under $370 million at the global box office. There’s one scene in particular everyone can remember…
Cameron Diaz And Ben Stiller Then
Cameron Diaz: Now
Cameron Diaz is one of the highest-grossing actresses in Hollywood and has featured in 15 films that have made more than $100 million at the global box office each. All combined, her films have made over $4 billion dollars. She herself is worth over $140 million. She’s known for many films, but perhaps none so much as Charlie’s Angels, in which she starred along with fellow angels Lucy Liu and Drew Barrymore. Serious star power.
Cameron Diaz Now
Ben Stiller: Now
Ben Stiller is without a doubt one of the best comedy actors of his era, and he has a $200 million net worth to show for it. All combined, his films have earned more than $6 billion at the worldwide box office, and a whopping 19 of them have earned more than $100 million. His show, named after himself, won him an Emmy. He has 127 credits but is best known for his Zoolander series.
Ben Stiller Now
Eva Mendes And Will Smith: Then
Get ready for the number three spot, it belongs to none other than Will Smith and Eva Mendes’ “Hitch.’ It came out in 2005 and raked in over $350 million at the global box office and had a sturdy production budget of $70 million. It follows a relationship expert whose expertise fails him when it comes to his personal relationship with the love interest played by Eva Mendes. It’s still a very popular film today.
Eva Mendes And Will Smith Then
Eva Mendes: Now
Eva Mendes shot to famed when she first appeared in the medical drama series “ER” all the way back in 1998. Following that, she’s gathered 42 acting credits, which include “Once Upon a Time in Mexico,” “Training Day,” and “A Night at the Roxbury.” Her films have racked up over one and a half billion dollars at the box office, and of course “Hitch” leads with $100 million. Her net worth stands at $15 million.
Eva Mendes Now
Will Smith: Now
Will Smith is undeniably one of the most accomplished actors Hollywood has. He’s seen success on the small and big screen and today has a net worth of over $350 million. He burst onto the scene with The Fresh Prince of Bel-Air”, running for six seasons, and has stacked up many blockbusters ever since. These days things have gone full circle, as he is currently a producer on the “Fresh Prince” inspired drama series “Bel-Air.”
Will Smith Now
Renee Zellweger And Tom Cruise: Then
This one is a certified 90s classic. Released in 1996, “Jerry Maguire” features Tom Cruise and Renee Zellweger, who meet after one of the characters has a crisis that leads to a reinvention. The film received an Oscar and Golden Globe nomination for Best Picture. The film was created on a sizeable budget of $50 million and went on to draw in over $273 million at the global box office. It still holds up today.
Renee Zellweger And Tom Cruise Then
Renee Zellweger: Now
Renee Zellweger has 45 acting credits to her name and includes such hits as “Chicago,” “Bridget Jones’ Diary,” and “Cinderella Man.” All added up, her filmography has generated over $2.74 billion at box offices around the world. For her part in the 2004 hit “Cold Mountain,” Renee Zellwegger took home one Academy award and was nominated for two more. Her net worth sits at a healthy $60 million, give or take a few million.
Renee Zellweger Now
Tom Cruise: Now
Tom Cruise is one of the biggest film stars of all time, and his name is synonymous with Hollywood. He has a hefty net worth of over half a billion dollars. He has many blockbusters to his name, almost too many to count. He is perhaps most well known for “Top Gun,” and has recently recaptured that magic in the long-awaited sequel, which recently smashed box office records. His films have made $10.12 billion.
Tom Cruise Now
Diane Keaton And Woody Allen: Then
Diane Keaton starred in the 1977 hit “Annie Hall,” playing the titular character. The film was also written and directed by Woody Allen, who stars as the comedian who falls in love with Keaton’s character. The film was awarded four Academy Awards and nominated for a fifth one. It also earned a Golden Globe. The film’s budget was a minuscule $4 million, but it earned just over $38 million total at the worldwide box office.
Diane Keaton And Woody Allen Then
Diane Keaton: Now
Diane Keaton is most well known for starring as Kay Adams in the much-loved “Godfather” series of films. Her 68 acting credits date back all the way to 1970 and include such classics as “Play it Again, Sam,” “Manhattan,” “Father of the Bride,” and “First Wives Club.” Her filmography has stacked up over $1 billion globally, and she herself has a net worth of over $50 million. She is still acting to this very day.
Diane Keaton Now
Woody Allen: Now
Woody Allen is regarded as one of the most acclaimed directors in cinema, and he has won four Oscars while also being nominated for over 12 more. His films include “Vick Cristina Barcelona,” “Midnight in Paris,” and “Manhattan.” All added up, his films have generated more than $1.2 billion at the American box office, and his net worth is over $80 million. His most recent film was released just recently, in the year 2019.
Woody Allen Now
Winona Ryder And Ethan Hawke: Then
Ethan Hawke and Winona Ryder’s films “Reality Bites” generated over $33 million at the global box office and was nominated by MTV for a Movie Award. It was directed by Ben Stiller and follows a group of 20-somethings figuring out life after leaving college. Although Stiller is known more for his acting, this film shows that he has directing chops too. Of course, it certainly wouldn’t be the same without Ethan Hawke and Winona Ryder.
Winona Ryder And Ethan Hawke Then
Winona Ryder: Now
From “Beetlejuice” to “Black Swan,” “Edward Scissorhands,” and “Girl Interrupted,” Winona Ryder definitely has one of Hollywood’s more varied resumes. She most recently found renewed success starring as joy in the hit Netflix series “Stranger Things.” She certainly has an affinity for the weird and strange. All added up, her films have earned $1.44 billion at the global box office, while her net worth is roughly $18 million. Not bad at all, Winona Ryder.
Winona Ryder Now
Ethan Hawke: Now
Ethan Hawke has had a long and varied career too. He’s known for his roles in “White Fang,” “The Purge,” and perhaps most famously, for his role alongside Denzil Washington in “Training Day.” Ethan Hawke has an impressive 81 acting credits to his name, dating back to 1985, and since then, his films have generated nearly one and a half billion at the box office. He is currently working on several films we’ll see soon.
Ethan Hawke Now
Patricia Arquette And Christian Slater: Then
“True Romance” is probably one of the most violent romantic films on this list, but what would you expect when you consider that Quentin Tarantino wrote it and released it in 1993. The film stars Patricia Arquette and Christian Slater as an in-love couple on the run from criminals. Even though the film has a cast of A-listers, it made just $12.28 million at the American box office. It is a cult classic film.
Patricia Arquette And Christian Slater Then
Patricia Arquette: Now
Patricia Arquette got her big break in 1987, starring in the third “A Nightmare on Elm Street” film. From there, she went on to star in such films as “Boyhood” and “Ed Wood.” More recently, she’s well known for her lead role in the hit TV show “Medium.” Her net worth is estimated to be about $24 million, and she most recently voiced Harmony’s mother in the latest animated “Toy Story” film, “Toy Story 4.”
Patricia Arquette Now
Christian Slater: Now
Slater is an 80s icon, that’s for sure, and he has an impressive 120 acting credits to his name since his role in “All My Children.” His list of films includes “Heaters,” “Kuffs,” “Mobsters,” “Pump Up the Volume,” and “Young Guns II.” He won a Golden Globe for his role in his most recent venture, the suspenseful series “Mr. Robot.” where he plays the titular character. His net worth sits at a comfortable $30 million.
Christian Slater Now
Alicia Silverstone And Paul Rudd: Then
Coming in quite far down the list as history’s 70th most successful romantic comedy is “Clueless,” which centers on a love story between a wealthy girl played by Alicia Silverstone and her humbler stepbrother, played by Paul Rudd. Something tells us this film may have been a little before its time, but it did earn more than $56 million when it was released to the world in 1995. Not bad at all, given the premise.
Alicia Silverstone And Paul Rudd Then
Alicia Silverstone: Now
Alicia Silverstone started her career in 1992 with a feature role in the series “The Wonder Years.” Later on, she landed starring roles in films like “Batman & Robin,” “The Crush,” and “Tropic Thunder. She also starred in server Aerosmith music videos. Her net worth is calculated to be roughly $20 million, and she received a Golden Globe nomination for her role in “Miss Match.” When all added together, her films have generated nearly $700 million.
Alicia Silverstone Now
Paul Rudd: Now
Paul Rudd has over 100 acting credits to his name, which include roles in films such as “The 40-Year-Old Virgin,” “I Love You, Man,” “Knocked Up,” and perhaps most famously, his tenure as “Ant-Man” in the Marvel cinematic universe. It’s probably thanks to Marvel that his filmography combined has grossed over $3 billion dollars at the global box office. He’s received seven MTV Movie Award nominations. Most recently, he starred in a new “Ghostbusters” film.
Paul Rudd Now
Drew Barrymore And Michael Vartan: Then
Falling even further down our list and taking the number 73 spot for the highest-grossing romantic comedy of all time is “Never Been Kissed,” starring Drew Barrymore and Michael Vartan. This movie follows a scrappy journalist on a mission to re-enroll in high school. When the film was released in 1999, it earned over $84 million at the global box office. Despite not being a classic, it does maintain a very small cult fan following.
Drew Barrymore And Michael Vartan Then
Drew Barrymore: Now
Drew Barrymore is practically Hollywood royalty, thanks to the fact that her grandfather is famed actor John Barrymore. The role that shot her to fame was in “E.T The Extraterrestrial,” despite the fact that she had starred in three films before it, although two of them were for TV. She’s known for many roles, including starring alongside another feature of this list, Cameron Diaz, in the much loved and followed “Charlie’s Angles” film franchise.
Drew Barrymore Now
Michael Vartan: Now
Michael Vartan is well respected, albeit lesser-known in Hollywood, for roles in “One Hour Photo,” “Alias,” “Bates Motel,”, and “Monster-in-Law.” Despite his relative fame, he doesn’t have as many acting credits to his name as others on this list. In fact, he only has 41 credits and a relatively humble net worth of about $8 million. He has been nominated for a total of three Teen Choice Awards as well as one MTV Movie Award.
Michael Vartan Now
Daryl Hannah And Tom Hanks: Then
“Splash” is a quirky comedy released in 1984 that featured the story of a romance between a human man and a mermaid. The film starred Daryl Hannah and Tom Hanks in the two leading roles. It was nominated for a single Oscar and just one Golden Globe and made an impressive $70 million at the American box office. It takes the number 53 spot on the list of the highest-grossing romantic comedies of all time.
Daryl Hannah And Tom Hanks Then
Daryl Hannah: Now
Daryl Hannah has a net worth of $20 million, as well as an impressive number of acting credits to her name. Over 90, in fact. Her career runs back to the 70s when she got her big break in “The Fury.” Since then, she’s starred in the well-received drama “Wall Street,” “Kill Bill,” “A Walk to Remember,” and “Blade Runner” alongside Harrison Ford. She still acts today, with some films that were released in 2018.
Daryl Hannah Now
Tom Hanks: Now
Tom Hanks is one of the biggest names on this list, with a diverse and very acclaimed set of acting credits. He’s starred in films such as “Dragnet,” “The Money Pit,” “Saving Private Ryan,” “Appollo 13,” “Philadelphia,” “Forrest Gump,” and “Cast Away.” All combined, his films have made more than $10 billion at the global box office, and his net worth is a whopping $400 million. These days he does more work as a producer.
Tom Hanks Now
Demi Moore And Patrick Swayze: Then
One of the most successful romantic comedies of all time is the film “Ghost,” which was the second-biggest film of 1990, just after the first “Home Alone” film. It made over half a billion dollars worldwide, on a budget of just $22 million. Moreover, it took how two Academy Awards and was nominated for a further three. It also won a Golden Globe. This film is probably best known for its famous pottery love scene.
Demi Moore And Patrick Swayze Then
Demi Moore: Now
Despite her success, Demi Moore has a humble 63 acting credits to her name, dating back to 1981. Her filmography includes such hits as “A Few Good Men,” “G.I. Jane,” and the raunchy “Striptease.” In total, all of her films have generated over $2 billion at the American box office. Her net worth is also a grand $150 million. Her most recent work is the TV adaptation of Adonis Huxley’s novel, “Brave New World.”
Demi Moore Now
Patrick Swayze: Now
Partick Swayze is an 80s heartthrob known for such gems as “Dirty Dancing,” “Road House,” “Point Break,” and “Red Dawn.” He has been nominated for three Golden Globes. Sadly he passed away back in 2009, but at that time, his net worth was over 40 million dollars. His memory lives on in all the films he’s left behind. “Point Break” is definitely his male fan’s favorite, while “Dirty Dancing” is the film for the ladies.
Patrick Swayze Now
Kate Winslet And Leonardo DiCaprio: Then
Let’s end off this list with what is perhaps the most classic pairing—Leonardo DiCaprio and Kate Winslet in the highest-grossing romantic film of all time, the historical drama “Titanic.” Not only is it the highest=grossing romance film, but it’s also the second highest-grossing film of all time, after another James Cameron film, “Avatar.” The film earned $2.19 billion at the box office and won 11 Oscars in total. A certified classic romance film.
Kate Winslet And Leonardo DiCaprio Then
Kate Winslet: Now
Unfortunately, Kate Winslet didn’t win the Academy Award for best actress in “Titanic,” but she did win it for her role in “The Reader”. She has just 63 acting credits, and those include roles in “Divergent,” “Revolutionary Road,” and “Eternal Sunshine of the Spotless Mind.” Thanks in part to Titanic, all of her films have grossed more than $4 billion at the worldwide box office, and her net worth stands at an incredible $45 million.
Kate Winslet Now
Leonardo DiCaprio: Now
Leonardo DiCaprio is a Hollywood titan, yet he won his first Oscar relatively recently for his role in “The Revenant.” His films have unsurprisingly earned about $7 billion at the global box office. Most surprising is the fact that he has just over 40 acting credits. DiCaprio certainly goes for quality over quantity. His net worth stands at an impressive $260 billion. One of DiCaprio’s most recent roles was in the latest Quentin Tarantino film.
Leonardo DiCaprio Now