There are few adversaries who hit home for the Caped Crusader as much as the duplicitous psychopath known as Two-Face. This fallen district attorney and friend of Bruce Wayne represents a casualty in
the heart of the Dark Knight, as he was one of the tortured souls that
Batman could not save and was the one who had all the potential to
further Batman’s goal of permanently cleaning up the corrupted city of
Gotham. Paired off with his deep psychological background and the
unique obsession with the realms of chance, we have one of the greatest
and most well-known of Batman’s enemies.

Per request from a friend who read my earlier Joker list, I decided to do another one focused on this rich character from the Batman mythology. So without further adieu, who is here the best of Two-Face
in the DC Animated Universe.

10. Unknowingly Defending Batman (The Strange Secret of Bruce Wayne from BTAS)

In an episode dedicated to guilt and blackmail, our caped crusader finds himself at the mercy of Dr. Hugo Strange, who has discovered his true identity and is auctioning off the information to the Penguin,
Joker, and Two-Face. Sabotaging the information to make it appear as if
Strange was hustling them, the disgruntled villains assault Strange and
take him on an airplane ride with plans to kill him (a little
far-fetched I know but it is a superhero show). Anyway, the golden
moment arrives when Strange attempts to save his life by giving them
the information, proclaiming that Batman is Bruce Wayne. In response,
Two-Face steps forward and refutes Dr. Strange as if he’s been given a
personal assault. He actually defends Bruce Wayne, claiming that there
is no way he is Batman as they had known each other as very close
friends in the past. From that point on, none of the villains lok twice
at that bit of information, and Batman’s identity ends up being kept a
safe secret.

This moment is great for a couple of reasons. On the one hand, it provides a great allusion to the depth of the friendship between Dent and Wayne, and how the multiple personalities and crime sprees do
nothing to change that. Also, this scene is great just from an ironic
standpoint as Two-Face actually saves Batman. Quite amazing I know, and
the reason why it is number 10 on the list.

9. His Own Worst Enemy (Multiple episodes of BTAS and TNBA)

One of the most interesting aspects of Two-Face’s character is that his personalities are at constant war with each other, sparking conflicts and obstacles that ultimately result in the failure of
Two-Face’s schemes or plans. This adds an unprecedented dimensionality
to the character, who could very well have been a cliched, cardboard
cut-out bad guy without it. It’s psychologically interesting, and
always entertaining to watch. Two instances in particular that are
noteworthy for this actually have whole episodes dedicated to them: Second Chance and Two-Face’s final appearance, Judgment Day.

In the former, Two-Face has undergone mass amounts of psychiatric therapy and has actually progressed to the point of making his own decisions without the coin. Deciding to undergo a surgery to repair his
face, he finds himself the victim of a kidnapping plot which is as
perplexing as it is spontaneous. It isn’t until the end of the episode
however that the culprit is Two-Face’s bad half, who kidnapped himself
in order to preserve his own existence within Harvey Dent. This
material is as rich as it sounds and very well pull together as a
whole. Even better though is the story from Judgment Day,
which involves a vigilante named the Judge and his violent crusade
against the Underworld. He eventually targets Two-Face, which involves
his knowledge of everything about Two-Face and staying one step ahead
of the super villain. After a final confrontation with Batman, it is
revealed that the Judge is Harvey Dent, whose personalities had split
into three, except the Judge persona was unaware of the other two. So
basically, Two-Face was attempting an unconscious but elaborate
suicide? Yes, and because of its sheer level of awesomeness, it takes
the Number Nine slot.

8. Creating Batgirl (Shadow of the Bat from BTAS)

As with the Number 10 slot, my Number eight pick has Two-Face unconsciously committing a good act and ultimately saving the Dark Knight. In this case, the act performed by Two-Face is providing the
indirect cause of Barbara Gordon taking up the Batgirl mantle. I won’t
go into a too much detail, but in short, Two-Face frames Gordon for
taking bribes with the intent to knock off Gordon, all so that Two-Face
can plant a stooge into the Commissioner’s chair while bringing in a
new syndicate to more efficiently run the rackets. With Batman and
Robin somewhat overwhelmed, and Gordon’s life at stake, his daughter
decides that the only way to get him safe in time is to do it herself.
On this note, she assumes the role of Batgirl, which ultimately leads
to Gordon’s safety and Two-Face’s incarceration.

As an indirect result of Two-Face’s criminal scheme, Batgirl became a permanent part of the Batman family and would go on to fight crime in Gotham City for years, saving Batman’s life multiple times in her
tenure. Because of the results associated with this act, this makes it
on the list at number eight.

7. Encounters with Poison Ivy (Multiple Episodes of BTAS)

Another interesting collection of moments involve Two-Face’s interactions with Poison Ivy, specifically after Harvey Dent has been transformed. After she took an attempt on his life through seduction
and plant toxins in her debut episode Pretty Poison, there
has been an animosity between the two that reveals itself in short but
memorable outbursts from Two-Face. The two best occurrences are in the
episodes Almost Got ‘Im (shown above) and Trial,
both of which jump start when Pamela makes a reference to their brief
relationship. In the former, Two-Face becomes quite angry and proclaims
that half of him wants to strangle her. Just like the smart ass she is,
Poison Ivy asks what the other half wants, to which Two-Face responds
“to hit you with a truck!” In the latter episode, in which Batman is
put on trial by the criminals in Arkham, Poison Ivy’s testimony
involves claiming that Batman should have let her kill Harvey Dent,
because the whole city would be better off. With that same evil grin,
Poison Ivy looks at Two-face (who plays the part of prosecutor) and
asks “wouldn’t we Harv?” In a priceless moment, Two-Face simply glares
at her and rapidly flips his coin, uttering retorts in Yosemite Sam’s
language for a while.

These amounts aren’t exactly common, but when they happen they are most amusing and give lighter dimension to a character steeped in darkness. Its fun, interesting, and well-deserving of the Number 7 slot.

6. Guilty….(Judgment Day from TNBA)

In his final appearance in the DC Animated Universe, Two-Face’s mind splits into a third personality, a separate one from the other two that becomes a violent vigilante known as the Judge. After attempting to
‘judge’ Two-Face as well as the Batman, the Judge is captured and thus
Two-Face is brought back to Arkham once again. The final shot of this
episode (as seen above) is worthy of note, as it fully displays this
inner turmoil of Harvey Dent in a highly creative way. Starting with a
closeup of Arkham, we are given a voice over of the Judge, who asks
Harvey Dent how he pleads in the case of “The People Vs. Harvey Dent.”
Looking broken, scared, and mentally shattered, Two-Face looks up at
the camera and repeats the word “guilty” as it zooms out away from him
until the episode fades to black.

While a certain fault of cartoons today is a failure to give a climactic ending, this episode certainly did for Two-Face. It was dark, brooding, and psychologically rich, equating to one of the best endings
of an episode in a series. For that, I gladly give it the Number 6 slot.

5. If He’s Robin, That Makes You… (Shadow of the Bat from BTAS)

As mentioned before in my Number 8 slot, Shadow of the Bat depicts the origin story of Batgirl, and how she stepped up to save her father and Batman when they were at the mercy of Two-Face. While I
recognized Two-Face’s involvement in this, there is a moment worthy of
greater mention that occurs in the second half of the story. With
Batman captured while in disguise, Two-Face takes him to an abandoned
subway station to get rid of him, as he had flipped on it before and
come out negative. Just before he unleashes his verdict however, Robin
swoops in to harm’s way to prevent his partner’s death, causing the
still-in-disguise Batman to yell “Robin look out!” After seeing Batman
duck behind a pillar and saying that, Two-Face approaches the pillar,
cocking his tommy gun. Realization and anger permeate his face as he
says “Robin? If he’s Robin, that makes you….” Fully understanding the
implication, Two-Face’s mouth and eyes twist towards an expression of
rage as he quickly lights up the entire pillar with machine gun fire,
keeping Batman pinned until two-Face ran out of bullets.

Granted, it’s a small moment, but it’s a powerful one filled with a great emotional outburst from Two-Face. It’s brief but tense, and the face that Two-face makes when he realizes he’s been duped is simply
priceless. It’s a great moment, and well-suited for the Number 5 slot.

4. Why Couldn’t You Save Me? (Two-Face from BTAS)

This next moment occurs in the second half of Two-Face’s origin story, appropriately titled Two-Face. technically, Two-Face doesn’t appear in this scene because of its reality as Batman’s nightmare, but it does show the impression that
Harvey Dent’s downfall left on the Caped Crusader, as it resembles the
tragedy of a friend that he not only failed to prevent, but indirectly
caused.

Seeing Harvey on a rickety bridge, Batman extends his hand and asks for Harvey to grab it, wishing to help. Dent, in a frightened but accusatory manner, relays his anger at how Batman failed to save him,
and buries his face in his hands. Upon lifting his face again, we see
Harvey Dent transformed into Two-Face, yelling at Batman “Now LOOK AT
ME!” Batman then attempts to step on the bridge, but it collapses,
causing Harvey to fall into an abyss. Before he disappears from sight,
Two-Face asks the question “Why couldn’t you save me?” To add insult to
injury, Batman looks down to see his parents, broken and saddened, as
they pitifully ask him the same question.

This nightmare reflects the turmoil that Two-Face’s transformation has wrought upon Bruce Wayne, as he is forced to take down a man who was once one of his closest friends. This is shown with the excellent
metaphorical visuals and script, and provides one of the most memorable
moments in the series as a whole. As such, it is well-deserving of the
Number 4 slot.

3. His Tragic Accident (Two-Face from BTAS)

It would be impossible to have a list of Two-Face’s greatest moments and not include the incident that sparked his criminal career, which is detailed completely in the first half of the two-part episode Two-Face. With
the stress of his re-election campaign and his war against crime boss
Rupert Thorne mounting, District Attorney Harvey Dent finds himself
suffering from violent outbursts; spawning from years of suppressed
anger and rage. Seeking psychiatric help for this condition, Dent
becomes the victim of a blackmail scheme from Thorne, who wishes to use
this information as a means to permanently sabotage Dent’s political
career. Confronting Thorne at an abandoned chemical plant, Dent snaps
and proceeds to fight Thorne and his men, until Batman drops in.

Running after Batman’s sudden appearance, Thorne is chased by Harvey Dent, who is unknowingly in the sights of one of Thorne’s men. Knocking the man down to disrupt the gunfire, Batman accidentally causes the
bullets to hit an electrical switchboard; ultimately resulting in an
explosion that decimates the left side of Dent’s face. Upon waking up
in the hospital, Harvey Dent realizes he has become half-man and
half-monster, his mind equally splitting to relfect that. From there,
he becomes the psychologically divided villain Two-Face, whose
existence is reflected by the flip of the coin.

This origin story is easily one of the best ones that the Batman mythology has to offer, and it is handled with well-deserved expert competence in writing, acting, and visual story-telling. It’s psychologically-rich
and spawned one of the greatest Batman villains in history. For that,
it gets the Number 3 slot.

2. Heads or Tails? (Second Chance from BTAS)

This was a moment that took me by surprise, as it single-handedly turned a solid episode into a great one, that is memorable to the point of never forgetting. I’ve gone through the main synopsis of the episode
in my Number 9 slot, so I won’t delve into anything but this scene
here, although the episode is certainly one worth checking out.

Long story short, Batman has been captured by Two-face and is tied up next to a bomb that is set to go off when Two-face presses the detonator. Flipping his coin to decide whether Batman will live or die,
the coin oddly lands on edge, causing Two-face to lose his composure
and try again. Sure enough the coin lands on edge, throwing Two-Face
into indecision, which allows Batman to escape his bonds and engage
Two-Face’s men. During this whole time, Two-Face continues to
repeatedly flips his coin, shouting “Heads or Tails, I have to know!
HEADS OR TAILS?” With each new flip, he begins to lose himself to more
desperation, until the coin starts to roll off the side of the
building, prompting Two-Face to dive after it.

This literally puts Two-Face in a cliffhanger, as one hand holds onto the building while the other holds onto the coin. Going to save him, Batman says that Two-Face has to choose between the coin or his
life. After a heart-pounding fifteen seconds, Two-Face drops the coin,
but uses his free hand to punch Batman in the face. This results in him
nearly falling to his death, till he’s saved by Batman. The episode
then ends with Two-Face seeing Bruce Wayne and smiling, telling him (as
Harvey Dent) how good of a friend he is for never giving up on him.

This scene picked apart Two-face’s psyche like no other, treating him and the coin as junkie to their addiction. It was rather brilliant, and the scene where Two-face chooses to drop the coin and attack Batman
was also wonderfully handled. This scene was fantastic and only just
falls shot of the Number 1 slot. However, it is more than qualified for
the Number 2.

1. Climax With Coins (Two-Face from BTAS)

In any story I read, film I watch, or video game I play, I have always preferred a strong ending to a strong beginning. I like endings with closure, power, and a real feeling of climactic force. As far as
the origin story of Two-Face is concerned, the first part of it
received a great conclusion, culminating in Harvey Dent’s
transformation into the villainous Two-Face. The conclusion of the
second part of the origin (as well as the origin story as a whole) is
just as powerful, delving into Two-Face’s character, and balancing out
the elements of tragedy and hope that permeates his being.

After finding his fiance Grace, Two-Face has her brought to his hideout, which is secretly being watched by Rupert Thorne’s men. After giving her a speech about his beliefs in chance, Grace attempts to
comfort Two-Face while Thorne bursts in with his thugs. Threatening to
kill him and Grace, Batman steps in and begins to engage Thorne’s men,
ultimately leading to their defeat. With Batman injured and Thorne
down, Two-face grabs a gun and points it at Thorne, saying that he
plans to take control of his life. Flipping a coin to decide whether to
kill Thorne or not, Batman quickly takes a box full of silver dollars
and throws them into Two-face’s path, causing him to lose track of the
coin. This throws Two-Face into a desperation similar to a drug addict,
as he screams for his coin while searching for it among hundreds of
similar coins. Reduced to tears, Two-Face embraces Grace and is brought
into custody. As Dent is being arrested, Commissioner Gordon asks
Batman if Dent will ever be cured. Batman, who has Two-face’s coin,
flips it into a fountain, where it lands with the good heads up. He
then completes the episode with this line of dialogue: “Where there’s
love, there’s hope Jim. But a little luck wouldn’t hurt.”

Providing a perfect conclusion to one of the best origin stories in the Batman mythology. It’s gripping, engaging, and sinks its teeth in you without ever letting you go. A great conclusion for one of Batman’s
greatest villains, and my pick for the Number 1 greatest Two-Face
moment.

Well there you have it guys: the ten best moments of one of Batman’s greatest friends, enemies, and tragedies. I hope you have enjoyed this, and until next time, stay gold.