All 7 Jack Nicholson Movies of the 21st Century, Ranked
An undisputed legend of Hollywood, Jack Nicholson has enjoyed one of the most decorated and illustrious careers film has ever seen, spanning seven different decades and amassing three Academy Award wins from a staggering 12 nominations. Ever hypnotic and defined by his mighty sense of screen presence, Nicholson is perhaps best known for his attention-grabbing work across multiple genres through the ’70s, ’80s, and ’90s, through which time he won all three of his Oscars and appeared in such classics as Chinatown, The Shining, and One Flew Over the Cuckoo’s Nest among many more.
However, Nicholson’s career continued into the new millennium, with the veteran actor appearing in seven films through the 2000s, leading up to his eventual retirement in 2010. Ranging from romantic dramas to somber comedies and even pulsating crime thrillers, Jack Nicholson’s filmography through the 21st century consists of career highlights and underrated gems, as well as some underwhelming low points. This list will rank every Jack Nicholson movie from the 21st century based on their quality, his performance, and the role they occupy in his larger career.
7
‘How Do You Know’ (2010)
Directed by James L. Brooks
There is a poignant touch of irony in the fact that a career as esteemed as Jack Nicholson’s effectively ended with a fizzle in the largely forgotten and critically derided comedy, How Do You Know. It follows Lisa (Reese Witherspoon), a determined softball star who finds her life in a whirlwind when she is cut from her team and finds herself falling in love with two different men. As she tries to navigate the next phase of her life, Lisa is torn between Matty Reynolds (Owen Wilson), a charismatic baseball pitcher, and George Madison (Paul Rudd), a businessman being investigated for stock fraud.
With Nicholson appearing as George’s father and the CEO of the business under investigation, the film presents a strong quartet of likable stars. Still, How Do You Know never stirs intrigue or even excitement with its love triangle premise and is stranded between tones that make for an underwhelming and flat viewing experience. It is incapable of escaping genre conventions, making for an uninspiring watch that is hardly worthy of its leading stars and is entirely undeserving of being Nicholson’s last-ever acting credit in cinema.
6
‘Anger Management’ (2003)
Directed by Peter Segal
Presenting Adam Sandler in his element yet somewhat detached from the erratic fervor of his movies from the ’90s, Anger Management delivers a zany experience that, despite featuring a handful of funny moments, remains largely stale. It follows Dave Buznik (Sandler), a typically mild-mannered guy whose simmering anger leads to an outburst that sees him placed in anger management with the renowned Dr. Buddy Rydell (Nicholson). When Dave’s situation worsens, Rydell is assigned to work with him full-time, seeing him accompany Dave at work and in his home life, where it becomes clear that Rydell might have some issues of his own.
The basic idea is strong, and the explosive and inspired pairing of Sandler and Nicholson has plenty of merit, but Anger Management ultimately errs in its execution. As expected, Nicholson is delightfully over the top, but the film’s complacency reaching for easy and lazy gags undermines what could have been a comedy gem. As such, it stands as one of the weakest pictures in Nicholson’s filmography and a relatively muted release in the context of Sandler’s career as well.
5
‘Something’s Gotta Give’ (2003)
Directed by Nancy Meyers
A refreshing rom-com that, while hamstrung somewhat by its adherence to genre conventions, still manages to soar because of its cast and its focus on budding romance between older people, Something’s Gotta Give is something of an underappreciated gem of 2000s romantic cinema. Nicholson stars as Harry Sanborn, a veteran music producer and prolific playboy whose new romance with Marin (Amanda Peet) annoys her mother, Erica (Diane Keaton). When a medical prognosis forces Harry and Erica to live under the same roof for a time, however, an unlikely romance begins to blossom.
Despite its familiar beats and its occasional straying into the realm of sitcom-style comedy, Something’s Gotta Give largely works as a smart, snappy, and considered portrait of the mystical allure of love. Nicholson and Keaton are both superb in their roles, bringing tremendous life and nuance to the film; her efforts resulted in an Oscar nomination. Something’s Gotta Give is one of the better American romantic comedies of the century thus far, even with its flaws.
4
‘The Bucket List’ (2007)
Directed by Rob Reiner
A movie that divided audiences and critics, The Bucket List is a well-intentioned comedy about friendship and embracing life. Edward Cole (Nicholson), an accomplished billionaire, and Carter Chambers (Morgan Freeman), a working-class mechanic, befriend each other when they are both diagnosed with terminal lung cancer. Refusing to succumb to despair by the unfortunate prognosis, the two men set out together in a bid to experience all the things they ever wanted to before they kick the bucket.
While it received condemnation from critics for being overly sentimental and purposefully manipulating the viewers’ emotions, average moviegoers were far more receptive to the film’s easy-going charms and touching exploration of friendship and mortality. It is far from flawless, but The Bucket List coasts by as a breezy and entertaining adventure that revels in Nicholson’s and Freeman’s aged camaraderie.
3
‘The Pledge’ (2001)
Directed by Sean Penn
An underrated neo-noir mystery thriller from the early 2000s that simmers as a richly atmospheric and delicately nuanced film, The Pledge is a grim tale of obsession and violence that comes to a bold and challenging conclusion. Jerry Black (Nicholson) is a veteran homicide detective on the cusp of retirement who agrees to participate in the investigation of a murdered girl. As he swears to the victim’s parents that he will find the murderer, Jerry soon grows obsessed with the case and goes to any length necessary to identify the killer.
While there is a procedural familiarity to the film’s progression, The Pledge always has a presence and a might that rises above mere genre regurgitation. Its success is due largely to Nicholson’s compelling lead performance and the grim tone that is both overbearing and intoxicating. Culminating with a shocking and riveting final act, The Pledge is a daring detective movie that contains what is perhaps Nicholson’s most underrated performance.
2
‘About Schmidt’ (2002)
Directed by Alexander Payne
A characteristically offbeat yet effective picture from writer-director Alexander Payne, and the film that contains the last Oscar-nominated performance of Nicholson’s career, About Schmidt is a divine marriage of drama and comedy that functions as a beautiful and moving character study. Warren Schmidt (Nicholson) finds himself adrift. Not only has his recent retirement left him aimless, but his wife’s sudden death after 42 years of marriage sees him stray towards seclusion. Disapproving of his daughter’s fiancé, he finds a temporary purpose as he sets out to postpone the marriage ceremony.
Its comedy is piercing and precise, with the story not only detailing the experiences of a man who realizes his time is running out but imposing his feelings of damnation and irrelevance on the viewer with a humor that is rife with dread as well. However, About Schmidt is fundamentally a testament to Nicholson’s astonishing talent. His portrayal of Schmidt depicts a man who is numerous things at once: tragic, disparaged, and somewhat prickly, yet entirely sympathetic and resonant. Indeed, About Schmidt is perhaps Nicholson’s finest achievement as an actor.
1
‘The Departed’ (2006)
Directed by Martin Scorsese
Not only the best movie Jack Nicholson has appeared in this century, but one of the greatest crime thrillers of all time as well, The Departed is an enthralling medley of deceit and violence that thrives with Martin Scorsese’s razor-sharp direction and its incredible ensemble cast. It transpires as dismissed police cadet Billy Costigan (Leonardo DiCaprio) is sent undercover to infiltrate Frank Costello’s (Nicholson) gang and identify a mole in the Boston Police Department. All the while, the mole, Colin Sullivan (Matt Damon), works to unearth the identity of the undercover cop to save himself.
Despite the fact that he didn’t receive an Oscar nomination for his performance, Nicholson is nothing short of arresting as the manic and unpredictable crime boss. His presence is paramount to making The Departed the unbearably tense and excellently tumultuous viewing experience that it is. A masterpiece of suspense and drama, The Departed is among the most engrossing gangster flicks of all time and a defining highlight of 21st-century cinema.
