Critical Reception and Legacy (Carlito's Way) Carlito's Way

The film opened to lukewarm reviews that treated it as a Scarface retread

Carlito's Way arrived on November 12, 1993, with Pacino coming off an Academy Award win for Scent of a Woman and De Palma reuniting with his Scarface star. Critics who expected another operatic rise-and-fall were puzzled by the film's quieter, more fatalistic register. The comparison to Scarface was inescapable and largely unfavorable in 1993. Peter Travers of Rolling Stone complained about Pacino's accent slipping into his Scent of a Woman southern drawl and faulted De Palma for "erratic pacing and derivative shootouts":

"What might have been if Carlito's Way had forged new ground and not gone down smokin' in the shadow of Scarface." — Peter Travers, Rolling Stone (1993) (paywalled, not verified)

Owen Gleiberman of Entertainment Weekly called the film "competent" but "unsurprising." The consensus was that De Palma was repeating himself. (wikipedia)

Roger Ebert recognized the mastery and gave it three and a half stars

Ebert stood apart from the lukewarm consensus, praising Pacino's restraint and Penn's transformation. He called the film one of De Palma's finest and singled out the set pieces, particularly the Grand Central escalator chase, as evidence of a director working at full command of his craft. Ebert recognized that the film was not trying to be Scarface but was doing something more melancholy: tracking a man who has already changed and watching the world refuse to accommodate it. (rogerebert)

CinemaScore audiences gave the film a B+, suggesting mainstream viewers responded more warmly than critics. The Rotten Tomatoes score settled at 85% based on 52 reviews, with a weighted average of 7.20/10 and the consensus: "Carlito's Way reunites De Palma and Pacino for a more wistful take on the crime epic, delivering a stylish thriller with a beating heart beneath its pyrotechnic performances and set pieces." (rottentomatoes)

Sean Penn's performance earned immediate recognition even from skeptical reviewers

Even critics who faulted the film's narrative praised Penn's disappearing act as Kleinfeld. The physical transformation (shaved forehead, perm, tinted glasses, nasal voice) was startling enough, but what earned sustained attention was Penn's ability to chart Kleinfeld's disintegration from charming fixer to coked-out murderer across the film's 144 minutes. Penn and Penelope Ann Miller both received Golden Globe nominations. (wikipedia)

The box office was modest and the film was quickly overshadowed

The film earned $37 million domestically and $64 million worldwide against a $30 million budget. It turned a modest profit but landed in a crowded fall season and was not the commercial event Universal had hoped for. Within months, the cultural conversation had moved on. The film did not have the lurid quotability of Scarface or the period glamour of The Untouchables. It was, by design, a quieter film about a quieter man, and quieter films disappear faster. (wikipedia)

The reappraisal began on home video and accelerated through the 2000s

Like many of De Palma's films, Carlito's Way found its real audience on VHS and DVD. The 2005 Ultimate Edition, which included deleted scenes and a De Palma interview, brought new attention to the film's craft. By the 2010s, critics who had dismissed it in 1993 were circling back. Producer Martin Bregman noted that some reviewers had retracted their negative positions. The film's reputation shifted from "lesser Scarface" to "one of De Palma's most personal and accomplished works." (wikipedia, crookedmarquee)

De Palma himself came to regard it as his best work:

"I can't make a better picture than this." — Brian De Palma, De Palma (2015)

Cahiers du Cinema named it one of the three best films of the 1990s

The French journal Cahiers du Cinema, the most influential critical publication in world cinema, placed Carlito's Way alongside Clint Eastwood's The Bridges of Madison County and Hou Hsiao-hsien's Goodbye South, Goodbye as one of the decade's three finest films. The selection validated what the film's growing cult following had argued for years: that the self-reflexive formalism and emotional restraint that American critics read as a retread in 1993 were in fact evidence of a master working at his highest level. (filmobsessive, crookedmarquee)

The film influenced hip-hop culture and generated real-world echoes

Carlito's Way penetrated hip-hop and street culture in ways its box office did not predict. Benny Blanco's name was adopted by drug dealers branding heroin packets in New York City. The film's dialogue, fashion, and fatalistic worldview were referenced across rap music, video games, and urban fiction. The 2005 prequel, Carlito's Way: Rise to Power, attempted to capitalize on this cultural footprint but was made on a fraction of the budget and lacked De Palma's involvement. Torres acknowledged it was not very good, though he praised Luis Guzmán's supporting performance. (mentalfloss, crimereads)

The film occupies a specific place in Pacino's career arc

Carlito's Way sits at a turning point. It arrived between the Oscar-winning bombast of Scent of a Woman (1992) and the tabloid excess of Heat (1995) and The Devil's Advocate (1997). Critics who returned to it noted that Pacino's Carlito was the last time he played quiet for an entire film, pitching his voice low and letting his eyes carry the performance rather than his volume. The restraint made the character's tragedy more devastating and gave the performance a quality that aged better than the louder work surrounding it. (crookedmarquee)

The Grand Central escalator sequence entered the canon of great chase scenes

The climactic chase through the subway and up the Grand Central escalators became the sequence most frequently cited in reappraisals. De Palma's sustained moving-camera work on the escalator, the editing challenge of making audiences forget how long the escalator actually runs, and the emotional payoff of Carlito reaching the platform only to meet Benny Blanco combined to produce what many critics now consider the most spectacular piece of filmmaking in De Palma's career. The sequence regularly appears on lists of the greatest chase scenes and action set pieces in cinema. (midwestfilmjournal)