Rihanna and Cara Delevingne
Both Cara and Rihanna are pretty glamorous in their own rights so it makes sense that the pair would get along. They’ve been spotted together sitting courtside at basketball games, attending gala’s, creeping into each other’s instagram’s and even starring in a big budget Hollywood film together titled “Valerian and the City of a Thousand Planets” where their friendship blossomed even more.
Entertaining Pair Potential: Cara is one of those crazy entertaining people because she’s always up to something ridiculous. Rihanna is one of the most famous global pop stars and you don’t get to be that without being super entertaining. The potential here is pretty high.
Priyanka Chopra and Meghan Markle
After having met at a womans event years ago, Priyanka and Meghan just clicked right away and have been friends ever since. Obviously since marrying Prince Harry it’s made hanging out a bit more difficult but they’ve said they still keep in touch through text and email. Just to add to the love fest between these two, almost any quote from either lady about each other is overwhelmingly positive
Entertaining Pair Potential: As far a fame goes, these are probably the most globally well known friends out of anyone on this list. The main issue here is that Meghan just isn’t the entertainment industry anymore so any potential projects aren’t possible. I’m going to slot them in the middle because of that.
Jennifer Aniston and Selena Gomez
This friendship started off in a very business like fashion. The two have the same manager and Aniston said she just wanted to take care of Selena. Since then, the two have hit it off without looking back. Selena, being the huge “Friends” fan that she is, was starstruck the first time she met Jennifer but eventually warmed up to her. Even now, Selena dresses up in the same iconic looks Aniston did in the 90’s.
Entertaining Pair Potential: One of the biggest pop stars in the world is best friends with one of the biggest movie stars in the world. Not sure what to tell you if you don’t see the entertainment there.
Snoop Dogg and Martha Stewart
I don’t feel like I’m making a stretch here by saying this is both the most random and most amazing celebrity friendship there is. After cooking on Martha’s show twice, Snoop said that the chemistry between the two was obvious. The next event they attended together was the roast of Justin Bieber which by this point is legendary. After that, they went on a run of recreating famous movie scenes that has taken the internet and world by storm.
Entertaining Pair Potential: It would be strange to rank the potential of this pair when they’ve already put out so much entertainment together. I guess we can rank the future potential for entertainment, and based off their previous work together, I have to put this as close to the top of the list as possible.
Kris Jenner and Jennifer Lawrence
Jennifer has been unabashed about her obsession with the Kardashians, unlike most of us however, Jennifer is an extremely prominent Hollywood actress which puts her in prime position to not only meet the Kardashian family, but actually create a real relationship. That is exactly what she did with Kardashian mom, Kris Jenner. Jen even made a cameo on “Keeping Up With The Kardashians” when Khloe tried to call her mom only to have J-Law answer the phone instead.
Entertaining Pair Potential: Like a lot of the people on this list, we wouldn’t know who either of these people were if they both weren’t very entertaining. J-Law is always a good time and Kris stars in one of the most successful reality shows on TV. Safe to say we watching these two wouldn’t get boring.
Kristen Stewart and Dakota Fanning
These two just love each other. Dakotta even said so while introducing Kristen at “ELLE’s Women in Hollywood Awards”, calling Kristen one of her best friends and a sister forever. Having starred in four “Twilight” movies as well to other films, the two have definitely had time to get to know one another intimately.
Entertaining Pair Potential: Both women have been acting since they were children so they both have lots of experience in the field of entertainment. More than that, after Kristen’s SNL hosting job a few years back, I’m willing to watch almost anything she does.
Kendall Jenner and Gigi Hadid
Probably the most far reaching friends social media wise, these famous model besties are seen everywhere with one another. Of course there’s been some reported drama which is to be expected considering Kendall is part of the Kardashian clan. Nevertheless, both Kendall and Gigi are by each other’s side through thick and thin.
Entertaining Pair Potential: The main entertainment these two could provide is tabloid headlines. They also have very highly followed instagram accounts which they make millions of dollars from which is entertainment in a sense. They’re going to have to rank near the bottom of the list though.
Emma Roberts and Lea Michelle
Lea and Emma starred together on Fox show “Scream Queens” and have been besties ever since. They’ve been spotted hanging out constantly and frequented each others Instagram account.
Entertaining Pair Potential: Having extensively followed “Glee” during its tenure, I know for a fact that Lea is entertaining as anyone. Now, Emma on the other hand I don’t have as much experience with. While I thoroughly enjoyed “We’re The Millers”, I’ve never seen any of the other stuff she’s in and therefore feel slightly under qualified to rate this pairs Entertainment Potential. Nevertheless, “Glee” makes the potential here too much to put this near the bottom.
Justin Timberlake and Jimmy Fallon
From their early days with Justin hosting SNL while Jimmy was a cast member, to today where the pair constantly perform in skits together on Jimmy’s “The Tonight Show”, this is one of Hollywood’s best bromances. The two originally met all the way back in 2002 where Jimmy was hosting the MTV awards for the first time and Justin was performing solo for the first time. They immediately calmed each other down and the rest is history.
Entertaining Pair Potential: The potential here is all the way to the moon. From what we’ve already seen, I don’t think a Jimmy and Justin pairing could do any wrong. They’ve done choreographed dances and imitated the Bee-Gees perfectly so whatever they do next will be amazing.
Keegan-Michael Key and Jordan Peele
Aside from starring, directing and producing huge Hollywood pictures, “Key and Peele”, as their known on the internet, have provided us with some of the most hilarious sketches and bits with their Comedy Central show “Key and Peele”. More recently they starred in the newest “Toy Story” together playing off of each other in a way only these two can.
Entertaining Pair Potential: I could probably listen to these two talk about anything. In addition to that, there isn’t a single form of media that this pair could put out that I wouldn’t consume. Basically, the entertainment potential here is pretty high considering their past.
Bette Midler and 50 Cent
This odd couple connected during a restoration project in New York. If any friendship can compete right with Snoop Dogg and Martha Stewart as most amazing and unexpected friendship in the history of humanity it’s this one. There’s just something about looking at two people who are complete opposites in every single way and realizing their friends.
Entertaining Pair Potential: If these two somehow found a way to make music together, I’m not entirely sure what the result would be but I do know it would be entertaining. To be honest, we should hope for a collab music wise just to see what the result would be. As far as entertainment potential, it’s reasonably high.
Reese Witherspoon and Mindy Kaling
These two became best friends after starring in “A Wrinkle in Time” together. Now they’ve given each other nickname and go on vacation together. Similar to a lot of these friendships, all it took was a few months of working together for these two to become besties, now they’re inseparable!
Entertaining Pair Potential: Mindy helped write “The Office” so I trust her almost 100%. The issue arises when pairing her with Reese, I don’t have any issues with Reese but their history together doesn’t bode well for entertainment. Although I haven’t seen “ A Wrinkle in Time” the reviews weren’t pretty, so I can’t endorse a purely entertainment based relationship.
Julia Roberts and George Clooney
Two of the most successful names in Hollywood, Julia and Goerge have been great friends since they starred in the “Oceans” series together. What started out as just fun and pulling pranks on one another, their relationship really blossomed when Julia was pregnant with twins and George went out of his way to help her.
Entertaining Pair Potential: These two have proven time and time again that they are titans of cinema. Both are able to play leads in Hollywood blockbusters and more than hold their own. It honestly feels weird to rank these two based on potential when they have such extensive track records but that’s what this section is so I’ll just put them near the top.
Julianne Hough and Nina Dobrev
The two were introduced by their mutual hairstylist over six years ago and have never looked back. Dobrev has stated that it feels like the pair have known each other since they were 2 years old! Nina was even a bridesmaid at Hough’s wedding to NHL player Brooks Laich where Nina jokingly asked if they could formally adopt her.
Entertaining Pair Potential: Nina is a vampire as evidenced by her role on “The Vampire Diaries”. Julianne is a professional dancer. Combining those two things together is entertainment, plain and simple.
Cameron Diaz and Drew Barrymore
Although they met in the 80’s and maintained a casual relationship, Drew and Cameron formed a friendship that stood the test of time and has left them more like sisters after starring in “Charlie’s Angels” together. They’ve helped each other through their tabloid filled lives and even served as bridesmaid at each others wedding.
Entertaining Pair Potential: I don’t have a gauge for the entertainment potential on this one. On one hand, these are two very successful members of Hollywood, on the other hand neither lady has done much of late with Cameron retiring from acting and Drew only doing TV. I’ll put them in the middle of the entertainment potential pack.
Tobey Maguire and Leonardo DiCaprio
While most of these friendships were sparked by being cast together in a film or meeting at an event, Tobey and Leonardo are childhood friends and have known each other for over 30 years. Even while competing for roles against each other, the two stayed best friends eventually leading to them starring in “The Great Gatsby” together.
Entertaining Pair Potential: This all depends on what role Leanardo portrays while hanging out with Tobey. Even though Tobey hasn’t played the role in over ten years, we all know he’s Spiderman, but Leonardo has the chance to make this sink or swim. Basically, I want a movie where Leanardo plays Jordan Belfort from “The Wolf of Wall Street” while Tobey is Spiderman.
Tina Fey and Amy Poehler
There isn’t much to say about these two that hasn’t already been said. Two of the funniest women in show business undoubtedly, these two have gone from improv classes in Chicago, to SNL, to starring in movies, to hosting the Golden Globes, all as a pair. These two just have comedic chemistry that you don’t often see.
Entertaining Pair Potential: Liz Lemon and Leslie Knope together. Mean Girls. SNL Weekend Update. Even on an individual level, there isn’t much you wouldn’t watch Tina or Amy do, but together as a pair? Shoot their potential into the stratosphere because there isn’t a single form of media they could create that wouldn’t be entertaining.
Matt Damon and Ben Affleck
Having grown up in the same Massachusetts neighbourhood, Matt and Ben have been friends since childhood. The quintessential Boston bromance, these two rose through the ranks together and ultimately won an Oscar for their work on “Good Will Hunting”. Although they haven’t worked together since that film in 1999, they have maintained a strong friendship.
Entertaining Pair Potential: It’s hard to know where to put these two. “Good Will Hunting” could have been lightning in a bottle when it comes to these two collaberating but based on both their extensive careers, I can’t imagine that’s likely. I feel like the potential here is on a different scale than others on this list. These two have evidenced that they can create Oscar winning content.
Kim Kardashian and Paris Hilton
This friendship has had a lot of ups and downs. While it may be hard to believe, Kim Kardashian wasn’t always a household name, in fact during this friendships hayday, Paris was the one who caught the eye of all the paparazzi. Over a decade, and multiple feuds later, the reality stars still call themselves friends.
Entertaining Pair Potential: The potential entertainment provided here is different than any other pair on this list. In terms of creative content, they would rank very low, but in terms of potential tabloid headlines and drama, they’d rank all the way at the top.
Jennifer Aniston and Courteney Cox
As far as friendships go, I’m pretty sure everyone knows how this one started. I also recognize the easy “Friends” puns I can make here due to the fact that Courteney and Jennifer are real life friends, but I am choosing not to. I’m sure it warms people’s hearts though to know that they’re favorite TV BFFs are also besties in real life and have looked into each others eyes to say “I’ll be there for you”… I’m sorry, I had to do one.
Entertaining Pair Potential: Having starred in one of the most successful and popular sitcoms of all time, there is obvious potential when it comes to these to working together. Solely due to “Friends”, a lot of people would tune in to see anything the pair make.
Adam Levine and Jonah Hill
The Oscar nominee and Maroon 5 frontman have been friends since junior high but they have shared more than normal friends do. Jonah’s older brother, Jordan Feldstein, was Maroon 5’s manager before his tragic passing in 2017. More than that, Jonah actually officiated Adam’s wedding!
Entertaining Pair Potential: Jonah Hill is hilarious and Adam Levine isn’t a slouch in the humour department either. The issue is that Adam doesn’t do movies, basically the only possible entertainment option here is an extremely well produced internet sketch. For that reason, I’m putting them straight in the middle of the pack.
Jennifer Lopez and Lean Remini
After initially being introduced 2004, Jennifer and Lean immediately became friends and took a liking to each other. Lean said that they’re similar upbringing made it a lot easier for the two to connect. When they were first introduced, Lean hoped that Jennifer would either be ugly, dumb or both because she thought Jennifer was too perfect.
Entertaining Pair Potential: They actually released a movie together in 2018 by the name of “Second Act” which I have not seen. Could be it’s the best movie in history, could be it’s the worst movie in history, I have no idea. For that reason, I have to put them in the middle of the pack.
Kevin Hart and Dwayne Johnson
Everyone knows that the true test of friendship is how far you can insult one another without offending the other person. If we’re going by that metric, Dwayne and Kevin are the best of friends. They’ve starred in multiple films together and seem like they’re having the best time any time they’re out in public, especially while insulting each other. It doesn’t hurt that they’re comedic timing works perfectly in tandem.
Entertaining Pair Potential: As evidenced, these two are extremely entertaining together. There’s a reason that individually, both Kevin and Dwayne are two of the most recognizable names in Hollywood. Together, they’ve made extremely entertaining movies, so I think they have to rank pretty highly.
Salma Hayek and Penelope Cruz
These spanish speaking besties have been friends since 2001 and starred in a movie together in 2006. They even have a nickname for each other, huevos [eggs]. They said it was a way to call each other lazy before they both had kids.
Entertaining Pair Potential: Hayek being from Mexico and Cruz being from Spain, these two have a lot of international potential. Being able to reach Latin America and Europe is a pretty big deal when it comes to entertainment so I think they should rank somewhere in the middle of the pack.
Naomi Watts and Nicole Kidman
Having met in Australia, these two blonde bombshells have been friends for over 35 years. They recently celebrated Naomis’s 50th birthday together! Even more recently, Naomi gushed over Nicole in honor of her 52d birthday. While all this is nice, I still find it extremely shocking that both these ladies are over 50!
Entertaining Pair Potential: Both these actresses have been nominated for Academy Awards, Nicole has even won once so they should be able to create some top level entertainment. When Oscars are involved, the entertainment potential jumps to the top, so I think it’s fair to rank them equally high.
Aziz Ansari and Jennifer Lawrence
From sleepovers to sightseeing in Italy to making extremely amateur short films with Chris Pratt and Amy Schumer, Aziz and Jennifer are the definition of friendship goals. Definitely two of the loudest people in Hollywood, it would probably be non stop fun hanging out with these two, no matter where you are.
Entertaining Pair Potential: If at any point these two decided to star in a buddy-buddy comedy together, I’m fairly confident everyone would come watch it. It would also probably be hilarious and extremely entertaining. Jennfier and Aziz are ranked right near the top.
Millie Bobby Brown and Maddie Zeigler
We have our first teen best friends here. Maddie is best known for her dancing performances in the music videos for Sia’s “Chandelier” and “Elastic Heart” while Millie is of course famous for starring in the hit Netflix show “Stranger Things”. Apparently when they had first met, Maddie hadn’t even seen “Stranger Things”, that’s how you know it’s a genuine friendship!
Entertaining Pair Potential: With Maddie’s dancing and Millie’s acting, I’m sure there are some movie or music video producers that could combine the pairs talents. Who knows? Maybe ten years from now both these girls are at the top of their fields, killing it. Because they’re both still young, I feel like we have to put them near the top of the entertainment potential scale.
Victoria Beckham and Eva Longoria
These two have been friends for a while now. Initially introduced through Victoria’s husband, David Backham and Eva’s ex husband, Tony Parker. Since then, Eva has inducted herself as a member of the Spice girls and made real relationships with Victoria’s family. Victoria was even a witness at Eva’s 2016 wedding. Safe to say they’re pretty close.
Entertaining Pair Potential: Victoria is a Spice Girl, that’s a lot of potential entertainment points. Pair with an award winning actress in Eva Longoria, you got yourself quite the entertaining pair. I think the safest place to them in near the top.
Eminem and Elton John
What started as a simple duet between the two music legends blossomed into a real and lasting friendship. During his struggles with drug addiction and stint in rehab, Eminem turned to Elton for support and advice, both of which the British icons happily indulged. While Eminem has been known to push buttons and offend, occasionally using homphobic slurs, Elton has always had his back.
Entertaining Pair Potential: When two legends in their respective field get together, there’s always the chance that it will be special. That’s no difference when it comes to these two. The potential for an all-time song is here so we have to put them almost at the top of the list.
Andy Cohen and John Mayer
You must be pretty good friends for the tabloids to assume your dating. That’s exactly what happened with these two, but they’re just good friends. John spent an entire 48 hours learning a song just to perform on Andy’s show for his 50th birthday.
Entertaining Pair Potential:The highest potential here is for John to be somewhat of an in house band on Andy’s show/ Obviously, this would be entertaining because John is extremely talented but it doesn’t have the potential as other pairs on this list. This goes near the bottom.