Chris Pine went from little-known actor to Hollywood heartthrob in mere months as a result of landing the role of Captain James T. Kirk in J.J. Abrams' Star Trek reboot, and since then he's built quite the expansive filmography. However, even prior to his "big break" as Captain Kirk, he had a well-established filmography featuring a lot of interesting projects.

Although his latest movie might not be his greatest movie, at least according to Rotten Tomatoes, Pine has managed to carve out a unique and varied resume over the course of his career.

Updated September 28th, 2022 by Jordan Iacobucci

Chris Pine's career has only grown in recent years, as the actor continues to take on interesting projects to further his already impressive legacy in Hollywood. With his latest feature film, Don't Worry Darling, setting the internet ablaze with its subversive plot and behind-the-scenes conflict, Pine is once again front-and-center, leaving his fans to once again comb through the best and worst films of his career.

Worst

Don't Worry Darling (2022) - 38%

Chris Pine as Frank in Don't Worry Darling.

Don't Worry Darling, Chris Pine's latest feature film, has certainly taken up its fair share of attention in recent months thanks to behind-the-scenes drama that did more for the film's publicity than its own marketing. In this subversive period piece, Pine portrays the leader of the mysterious Victory Project, which one housewife (portrayed by Florence Pugh) begins to question, leading her to conflict with the men of the town.

Though Don't Worry Darling attempts to be a subversive psychological thriller, it ultimately waits too long to unravel the mystery at its center, leaving audiences somewhat underwhelmed by the ultimate resolution. Though the film was generally panned by critics, the performances of both Pugh and Pine were hailed as the best parts of the overall disappointing movie.

Horrible Bosses 2 (2014) - 35%

Chris Pine in Horrible Bosses 2

After the surprising success of the original film, Horrible Bosses 2 saw the main cast of characters explore yet another HR nightmare as more terrible superiors made their way into the workplace. In this sequel, Pine portrays Rex Hanson, the son of a corporate executive whom the main characters resolve to kidnap and hold for ransom, leading to plenty of slapstick comedy and mishaps along the way.

Though the original wasn't much to write home about either, Horrible Bosses 2 managed to be even worse than its predecessor, bringing a bland flavor to its already irreverent and uncomfortable sense of humor. The film was quickly met with disparaging reviews by critics, leaving the franchise without the possibility of a third installment.

Smokin' Aces (2006) - 30%

A promo photo for Smokin Aces

Released in 2006, the action/comedy film Smokin' Aces follows a series of hitmen as each tries to claim the million-dollar-bounty placed on the head of Buddy "Aces" Israel, a shoddy magician and part-time gangster, by a mob boss who doesn't want Israel's knowledge to get to the wrong people.

Despite its impressive cast, the film's convoluted storyline and bad-taste humor ruined its chances with critics, and its Tomatometer rating sits at just 30%. Audiences, however, gave the film a much more positive 62% score.

The Princess Diaries 2 - Royal Engagement (2004) - 26%

Chris Pine and Anne Hathaway in The Princess Diaries 2

Pine's first major role was also a bit of a disappointment. Released in 2004, The Princess Diaries 2 - Royal Engagement follows Mia, a princess who learns that, as a result of long-standing tradition, she must be married within the next month to become her kingdom's Queen.

The film's leads, including Anne Hathaway, Julie Andrews, and Pine himself, received some praise, but its screenplay and story were critically panned, resulting in a "certified rotten" Tomatometer rating of just 26%.

This Means War (2012) - 26%

Chris Pine and Tom Hardy's characters wear suits in This Means War

The 2014 action comedy This Mean War takes the spy genre and infuses it with a heaping of trite rom-com fare, including the classic "two guys fighting over one girl" trope, with Chris Pine and Tom Hardy playing the roles of said guys.

This isn't necessarily a bad concept on its own, but critics also found issues with the film's plot, dialogue, and action sequences, and its embarrassingly low rating of 26% unfortunately proves that even the star-studded trio of Chris Pine, Tom Hardy, and Reese Witherspoon couldn't save it from Tomatometer oblivion.

Blind Dating (2006) - 25%

Chris Pine in Blind Dating

Released in 2006, the rom-com Blind Dating follows a blind man (played by Pine) who tries to find love. This film, which came off as somewhat insensitive, is largely forgotten by fans of Chris Pine, who prefer not to hold its poor quality against him.

Critics saw the film as badly plotted, badly paced, and just not that good of an idea in general. Rotten Tomatoes describes it as "uneven" and "unmemorable", and it currently has a Tomatometer score of just 25%.

Just My Luck (2006) - 14%

Chris Pine and Lindsay Lohan in Just My Luck

The 2006 rom-com Just My Luck stars Lindsay Lohan as Ashley, a Manhattan girl who's pretty, popular, and never in short supply of luck. After she kisses the "unlucky" Jake Hardin (Pine), however, their roles are switched, and she becomes the "unlucky" one.

A decent premise, perhaps, but critics noted that the film itself was unimpressive and uninteresting, and fell victim to a wide variety of trashy teen rom-com tropes. Just My Luck currently has a rating of just 14% on Rotten Tomatoes.

Best

Star Trek: Beyond (2016) - 86%

Captain Kirk in Star Trek Beyond

Star Trek: Beyond is the third and, so far, the final entry in the rebooted Star Trek franchise in which Chris Pine stars in the iconic role of Captain James T. Kirk of the U.S.S. Enterprise. The sequel sees the crew journey to an unknown planet whilst coming to appreciate the lives they'd taken for granted upon the Enterprise.

Though Star Trek: Beyond received higher critical praise than its immediate predecessor, its box office numbers were a severe dip from the previous two films. The film's financial failings largely brought an end to Stark Trek's cinematic releases, keeping Pine from a long-running franchise that might have proven especially lucrative.

Unstoppable (2010) - 87%

Denzel Washington and Chris Pine walking by a train in Unstoppable

Unstoppable is an action film based on true events in which a runaway train nearly causes incredible havoc. Chris Pine and Denzel Washington portray a train conductor and railroad engineer, respectively, who are tasked with stopping the train before it crashes.

Unstoppable was praised for its heightened sense of tension and the performances of its two leads. As one of Pine's early hits, the film served as a catalyst for many of his future action-hero roles, which would become a staple of his future career.

Stretch (2014) - 88%

Patrick Wilson in Stretch

The wacky comedy-drama Stretch, released in 2014, stars Patrick Wilson as a limousine driver who takes on an eccentric -- and potentially dangerous -- client (Pine) in order to satisfy a gambling debt.

The film received critical praise for its cast and humor and currently holds an 88% rating on Rotten Tomatoes. Though the film had high numbers critically, it has had little lasting presence on Pine's career or on the film industry as a whole.

Wonder Woman (2017) - 93%

Chris Pine as Steve Trevor and Gal Gadot as Wonder Woman

2017's Wonder Woman follows Diana, an immortal Amazon warrior-princess, as she tries to stop one of history's greatest conflicts -- World War I. Accompanying her is Steve Trevor (Pine), a good-hearted pilot who meets Diana after crash-landing on her hidden island home.

Wonder Woman received positive reviews from critics for its story, characters, visual effects, and directing, and currently has an outstanding 93% rating on Rotten Tomatoes. The film remains one of the highest-regarded entries in the otherwise troubled DCEU, though its 2020 sequel would not be so well-received.

Star Trek (2009) - 94%

A promo photo from Star Trek 2009

Helmed by Lost visionary J.J. Abrams, 2009's Star Trek served as a much-anticipated reboot of its beloved franchise. Given the film's monumental cast (including such big-name people as Chris Pine, Zachary Quinto, and Zoe Saldana), fans and critics both came in expecting a lot.

Ultimately, the film received critical praise for its story, acting, humor, characters, and special effects, and spawned a third series of Star Trek films. It currently holds a 94% rating on Rotten Tomatoes, finding enthusiasm from audiences as well, with the film becoming one of the highest-grossing projects in Pine's career.

Spider-Man: Into the Spider-Verse (2018) - 97%

Chris Pine's Spider-Man in Into the Spider-Verse

2018's Spider-Man: Into the Spider-Verse follows Miles Morales, a teenager living in Brooklyn who discovers he's the next Spider-Man. After a dimension-collider brings a series of misplaced Spider-people to his doorstep, Morales has to figure out how to save them -- and all of Brooklyn -- while still learning how to use his powers.

The film won several awards, including the Oscar for Best Animated Feature, and received critical praise for its story, characters, animation, and humor. It currently holds a 97% rating on Rotten Tomatoes, with audiences impressed by the film's dedication to becoming one of the best cinematic depictions of Spider-Man ever.

Hell or High Water (2016) - 97%

Brothers looking into the distance in Hell or High Water

2016's Hell or High Water is an Old-West-style crime film following two brothers (played by Pine and Ben Foster) who end up on the run from the law after they rob a series of banks to pay off the debt on their family ranch.

The film's well-executed drama and admirable acting won it many accolades, as well as near-universal critical praise; it currently holds a 97% rating on Rotten Tomatoes. Ultimately, any of Pine's films following Hell or High Water failed to live up to its gravitas or prestige, making the 2016 film the very best in the actor's still-blooming filmography.

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