Batman's most iconic rogues' gallery obsessed with duality and leaving fateful decisions to the flip of a coin.

Dent doesn't typically boast any superpowers and instead adds to the litany of sympathetic DC villain. Throughout his numerous adaptations, some movies and TV shows hit the mark with Dent better than others.

13 Andy Daly In Harley Quinn

Harley Quinn's Dent Doesn't Embody Many Hallmarks

Unlike many Two-Face adaptations, the version that appears in the critically acclaimed Harley Quinn show plays a relatively central role. His involvement ramps up in season 2 when he becomes a primary antagonist to Harley Quinn and s up with the Injustice League. Unfortunately for Daly's Dent, the adult-themed and exaggerated comedy of Harley Quinn works against his characterization.

Harley Quinn's Harvey Dent is such an outright villain that he routinely betrays his fellow villains. This flies in the face of what makes Dent so compelling, as he is typically in conflict with his desire to do good when carrying out acts of evil. Instead, Harley Quinn takes the Two-Face moniker literally and ascribes the name to the personality, turning him into a caricature that - while hilarious - does not speak to Harvey Dent's true character.

12 Yuri Lowenthal In Gotham By Gaslight

Victorian Era Harvey Dent Is Overtly Unlikable

Gotham By Gaslight explores the Batman mythos in a Victorian Elseworlds setting and centers around the crimes of Jack the Ripper. Dent appears as an old school friend of Bruce Wayne and acts as the movie's secondary antagonist. Unfortunately, he never undergoes a Two-Face transformation and is portrayed as outwardly villainous nonetheless. While Yuri Lowenthal does a great job with the voice, it is not enough to excuse the departure from Two-Face's origins.

Gotham by Gaslight is loosely based on the 1989 one-shot graphic of the same name.

This version of Dent shows very few redeeming features, as he is also willing to throw his old friend under the bus out of jealousy - again embodying a two-faced personality, but not Two-Face's. He is shown to be a misogynist womanizer with no true desire to fight for justice. Both of these factors detract from both his core comic book origins and the version of Dent portrayed in the Gotham by Gaslight one-shot graphic novel.

11 Harry Lawtey In Joker: Folie Á Deux

Joker 2's Harvey Dent Is Loose And Less Explored Interpretation Of The Character

Warning! This entry contains spoilers for Joker: Folie à DeuxJoker: Folie à Deux is as the Assistant District Attorney before any attack or accident scars his face and turns him into Two-Face. His role is pivotal but minor as he is the one to doggedly pursue the death penalty for Arthur Fleck and lead the charge against him in his very public trial. He would ultimately fall foul of the car bomb that grants Fleck a moment of freedom, leading to one side of his face being lacerated by the blast - though this would be the last seen of Lawtey's Dent.

Despite his pursuit of justice against Fleck, this version of Harvey Dent comes across as a particularly smarmy character - though it is hard to say how much of his characterization is part of Fleck's delusion - seeking to further his own career. This works against his portrayal as the most compelling versions of Dent typically fall from grace as a likable and more overtly virtuous character. The fact that Lawtey's Dent does not boast much screen time (and, therefore, character development) compounds this.

10 Nicholas D'Agosto In Gotham

Gotham's Harvey Dent Is Frustratingly Never Turned Into Two-Face

Nicholas D'Agosto's Harvey Dent plays an important role in Gotham in earlier seasons as the eponymous city's Assistant District Attorney but once again never makes the full transformation into Two-Face. He makes only minor appearances later in the five-season show but is a close ally of Jim Gordon in earlier episodes. The two work together in their attempts to bring justice and peace to Gotham - ideals in which this version of Dent seems to truly believe.

Instead, Dent's duality and dark side are merely hinted at in the form of outbursts and choice lighting throughout his appearances.

While D'Agosto's portrayal of a more virtuous version of Harvey Dent before his Two-Face transformation is laudable, it is frustrating that this character was never fully transformed. Instead, Dent's duality and dark side are merely hinted at in the form of outbursts and choice lighting throughout his appearances. Due to being underutilized in later seasons, this version of Dent feels like wasted potential.

9 James Remar And Richard Moll In Batman: The Brave and the Bold

Batman: The Brave And The Bold Features A Lighthearted And Simplified Two-Face

Batman: The Brave and the Bold is another lighthearted take on the Caped Crusader, with a rogues' gallery that leans into the more theatrical side of their characterization. Two-Face is no different as he typically appears as part of an ensemble of Batman villains, but still displays his penchant for duality and his coin. His appearances throughout the show are relatively sporadic in this manner.

Remar and Moll's takes on the character are simplified yet still comic-accurate and undeniably fun. Batman: The Brave and the Bold's tone does not quite match the inherently tragic character of Harvey Dent, yet Remar and Moll make it work nonetheless with an over-the-top depiction of the villain that still maintains his most iconic characteristics. This is also a memorable, green-skinned version of Two-Face that works well with the show's distinctive art style.

8 Diedrich Bader In Batman: Caped Crusader

Batman: Caped Crusader Flips Harvey Dent's Defining Features

Batman: The Caped Crusader is a t venture by JJ Abrams, Matt Reeves, and Batman: The Animated Series head producer, Bruce Timm, that takes a more mature approach to animated Batman offerings. Set in the 1940s, it is reminiscent of Batman's roots while delivering fresh but welcome new spins on his rogues' gallery. Harvey Dent is a recurring character throughout the series as a smarmy, corrupt DA who becomes central to the series finale as a heroic figure.

Dent's disfigured side is typically representative of his villainous side in DC Comics and beyond, whereas the opposite is true in Batman: Caped Crusader.

Diedrich Bader's take on Harvey Dent is notably different from typical depictions insofar as his facial disfigurement makes him less villainous. Dent's disfigured side is typically representative of his villainous side in DC Comics and beyond, whereas the opposite is true in Batman: Caped Crusader. Instead, Dent turns from a smarmy, corrupt politician in the lead-up to his acid attack to an antihero in season 1, episode 10. This contextualization is a breath of fresh air as it does not fundamentally warp the duality that Dent embodies.

7 Billy Dee Williams In Batman & The LEGO Batman Movie

Both Roles Were Minor But Memorable

Billy Dee Williams has portrayed Harvey Dent twice in DC media. His first and most significant was as Harvey Dent in 1989's Batman starring Michael Keaton in the titular role. The City of Gotham's District attorney plays a minor role as a straight-laced champion of justice against organized crime in Gotham. While he does not transform into Two-Face in Batman, Billy Dee Williams' role in The LEGO Batman Movie pays off the role that could have been - though it is, again, very minor and decidedly more comedic.

Billy Dee Williams' portrayal of Harvey Dent in Batman was well-received for his charm and confidence, though he would never be afforded the chance to flesh this out in a later installment. Despite his minor role, Williams perfectly conveyed a pre-transformation Dent as an idealistic and competent DA with virtuous goals, perfectly setting up his transformation down the line. There was a high demand for Billy Dee Williams to return to the role after his Batman Forever snub, which speaks volumes about what he brought to the role.

6 Tommy Lee Jones In Batman Forever

Tommy Lee Jones' Frenetic Portrayal Of Harvey Dent Is Unforgettable

The lurid motifs of 1995's Batman Forever were a stark departure from Tim Burton's gothic take on the Batman mythos, which was encapsulated by the movie's villainous double-act, Two-Face and The Riddler. The movie sees Two-Face fully embody his villainous persona from the jump, being introduced with a characteristic flip-of-the-coin. His exceptionally campy depiction of the character who is hellbent on murdering Batman for relatively superficial reasons, has yet to be equaled outside of animations.

While Tommy Lee Jones' Two-Face is a somewhat controversial interpretation, he still displays many of his most important hallmarks.

While Tommy Lee Jones' Two-Face is a somewhat controversial interpretation, he still displays many of his most important hallmarks. His obsession with duality and luck is still at the forefront of this flamboyant portrayal, which, when combined with his preoccupation with flipping his fateful coin, is at least somewhat comic-accurate. While this version of Two-Face may rub some fans the wrong way, there's no denying that Jones' portrayal is still incredibly memorable.

5 Misha Collins In Gotham Knights

Misha Collins' Harvey Dent Was A Highlight Of The Show

Gotham Knights takes place in Gotham after Bruce Wayne's death, leaving a group of young vigilantes to pick up the slack. Dent plays a central role in the series, which depicts his slow transformation into Two-Face across 13 episodes. While this transformation is finalized in the series finale, Misha Collins' portrayal of Harvey Dent shows the slow but inevitable decline of his moral character before being disfigured by acid pushes him over the edge.

The relatively poor reception to Gotham Knights puts Misha Collins' Harvey Dent in a precarious position, but his portrayal remains a series highlight. While he does not embody the role of a Batman villain specifically, the characterization of Harvey Dent as a genuinely well-meaning District Attorney struggling with a dark side that steadily takes over as the series progresses is worthy of note. Unfortunately, Collins was unable to properly deliver a take on Two-Face before the show's cancelation.

4 Willaim Shatner In Batman Vs. Two-Face

William Shatner Delivers Some Brilliant Voice Acting

Batman Vs. Two-Face is a continuation of the Batman show of the 1960s with Adam West in the starring role. The straight-to-video animated movie depicts a particularly troubled version of Harvey Dent who is at odds with his Two-Face persona, culminating in a battle for control between the two. Despite featuring a tortured version of Dent, it maintains the campy tone of the 1960s Batman franchise, featuring such set pieces as the "Evil Extractor," which extracts liquid evil, and a climactic final bout involving a bi-plane.

Batman Vs. Two-Face was Adam West's final appearance as Batman and was released posthumously.

Despite the over-the-top and whimsical content in this appearance, Shatner delivers a surprisingly touching take on Harvey Dent in Batman Vs. Two-Face. The movie actually delves refreshingly deep into the character and Harvey Dent's struggle to wrest control from an evil personality in Two-Face. Shatner's performance is especially praiseworthy, helping to hammer home the duality of Dent's dual personalities with a strong vocal performance that makes both sides distinct.