It seems that in Hollywood it’s not all that unusual for siblings to want to work in the same profession, with many high-profile acting siblings finding success in the industry in their own rights, from the Olsen sisters and the Hemsworth brothers to Emilio Estevez and Charlie Sheen. Whether or not there are any hidden sibling rivalries behind the scenes, more often than not it seems that famous siblings are very supportive of each other’s careers.

A sibling bond is hard to break, and when it comes to acting, this bond is often demonstrated by the family members choosing to work together. The result has led to some iconic instances of on-screen sibling collaborations. Below we take a look at 7 times actors have starred in movies alongside a sibling.

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7 Casey and Ben Affleck — Good Will Hunting

     Miramax Films

With both Casey and Ben Affleck being involved in various aspects of filmmaking aside from acting, the two have crossed paths many times in a working capacity. Movies where they actually act alongside each other are actually fairly scarce, considering the pairs’ extensive catalogs. One of the earliest and most notable collaborations, however, has got to be the award-winning Good Will Hunting. With Robin Williams playing against type and wowing audiences with his Oscar winning performance, Ben Affleck and Matt Damon, who also co-wrote the movie together, also received universal acclaim for their performances. Whilst Casey’s role wasn’t as prominent as Ben’s, it was also widely praised and has been cited as an early example of the capabilities the younger Affleck would flex in larger roles later in his career.

MOVIEWEB VIDEO OF THE DAY

MOVIEWEB VIDEO OF THE DAY

MOVIEWEB VIDEO OF THE DAY

6 Maggie and Jake Gyllenhaal — Donnie Darko

     Flower Films

After appearing together in two of their director dad Stephen’s films — 1993’s A Dangerous Woman and 1998’s Homegrown real-life brother and sister — Jake and Maggie Gyllenhaal appeared as on-screen siblings in 2001’s highly acclaimed cult favorite science fiction psychological thriller Donnie Darko. The movie showcased the pair’s obvious acting abilities and helped them achieve worldwide recognition and truly launch their respective careers.

5 John and Joan Cusack — High Fidelity

     Touchstone Pictures

The beloved Hollywood siblings have been appearing in movies with each other since the early-80s. Early on in their careers, many of the roles may have been fairly small in stature, but that soon changed as they both rose to prominence in their own rights throughout the 90s and 2000s. One of their most notable and well-loved collaborations is most likely 2000’s cult classic High Fidelity. Both siblings shine in this romantic, coming-of-(middle?)-age comedy, focused on the life of a record store owner (John) as he looks back at his top five break-ups (including one in progress), with Joan playing a mutual friend of both trying to stay neutral during said break-up.

4 Macaulay and Kieran Culkin — Home Alone

     20th Century Fox

The Culkin family is full of entertainers. Father, Kit, was a stage actor and had always hoped his kids would make it big. Acting as their manager, per Vanity Fair, the three siblings Rory, Kieran, and Macaulay all followed in his footsteps into the world of acting. Unless you’ve been living under a rock, you will be familiar with Macaulay Culkin, who in the late-80s and early-90s had become the biggest and most bankable child star on the planet. Not one to miss an opportunity, Kit negotiated that younger brother Kieran star alongside Macaulay in his biggest movie, Home Alone, albeit in a far smaller role. While his role as Macaulay’s cousin didn’t get that much airtime, it was a stepping-stone towards the successful acting career Kieran now has. Similarly, Macaulay’s brother Rory appeared in a smaller role alongside Macaulay in the movie Richie Rich, and has gone onto to thrive in his own right.

3 Mary-Kate and Ashley Olsen — It Takes Two

     Rysher Entertainment

Mary-Kate and Ashley, better known as the Olsen twins, started sharing the screen together from pretty much the day they could talk. Starring in countless TV shows and made for TV movies, the pair ruled the small screen, quickly becoming among the wealthiest women in the entertainment industry when they were merely tweens. Their big screen output was less plentiful, but they did make it to the theaters on at least a couple of occasions with the first being 1995’s It Takes Two. In terms of plot, the film shared a number of similarities to The Parent Trap, which went on to be remade a few years later with Lindsay Lohan and overshadowed It Takes Two in almost every way conceivable. The Olsen twins’ impact on entertainment, however, is nothing short of legendary and is still being felt to this day.

2 Luke and Owen Wilson — Bottle Rocket

     Columbia Pictures

Both members of the ‘Frat Pack’ a group of comedy actors, including Jack Black, Ben Stiller, and Will Ferrell, that rose to prominence in the late-90s and early-2000s for their rambunctious comedies, Luke and Owen Wilson have starred in a few movies together. The first and probably most significant was Bottle Rocket. Not only was it the major acting debut for both the brothers, but it also marked the first time they worked with director and future long-term collaborator, Wes Anderson. The film also marked Anderson’s directorial debut. The quirky comedy was a minor hit on the indie circuit, but gradually developed a cult following and paved the way for both the Wilson brothers’ and Anderson’s long and successful over lapping careers in the industry.

1 Shawn and Marlon Wayans — Scary Movie

     Wayans Bros. Entertainment

The Wayans family is almost an entire entertainment empire in itself consisting of multiple generations of writers, directors, producers, and actors. While it’s not unusual to witness multiple family members collaborating with each other on numerous projects, it’s brothers Shawn and Marlon whom you’d most likely catch sharing the screen together. The pair even starred in the sitcom The Wayans Brothers named after them in the 90s. The siblings have appeared in numerous movies together, specializing in over-the-top absurdist humor and parody and spoof flicks. By far, their most successful offering was 2000’s horror spoof movie Scary Movie, which was a huge box office hit, spawned multiple sequels, and inserted the duo firmly in the mainstream consciousness.