In the annals of history at DC Comics, the Teen Titans stand the test of time. Whether you are a fan of their legendary ‘80s run with Marv Wolfman and George Perez or you became a fan with the more recent Teen Titans Go animated show, these characters have become household names. In fact, they are about to come into households in a whole new way when they hit DC’s new digital streaming service in a live action show next year. Of course, even though they have had many highs, the team has also had some very low points, too.

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Just to clarify, some of these moments take place in the later years for the characters when they are simply “Titans,” “New Titans,” or have moved on for a period from the team. Unsurprisingly, choices regarding relationships and the commitment to said relationships have been a reoccurring problem for the team. Many Titans have had to deal with what they or those they love become in the future, and there are often grave consequences that come along with that. Being a Teen Titan means that there is always a measure of drama to be expected, but how dramatic can it get? You're about to find out!

SPOILER WARNING: This article contains spoilers for multiple recent Titans related titles.

15 DAMIAN KIDNAPS HIS OWN TEAM

15 Damian kidnaps

Rebirth brought with it a new group of Teen Titans. This time, they were brought together with a purpose by none other than current Robin, Damian Wayne. Damian had a looming issue with his grandfather Ra’s Al Ghul and needed help to deal with it. Rather than approach them all in a diplomatic fashion, Damian decided to do what he normally does and go about things his own way.

He systematically exploited all of their weaknesses, taking down each member of his choice for the new team. Not only that, but he followed it all up by then daring them all to join him facing down one of the most dangerous villains in the world and giving them backhanded compliments. He was being a jerk, but that's just Damian.

14 AT THE MERCY OF DICK

14 mercy action

Dick Grayson and Barbara Gordon go back a long way. They grew up together fighting alongside Batman, and like any two young, attractive people might, developed feelings for each other. Then their lives took different paths. Dick led a new team of Titans and met Starfire, a beautiful alien princess and the two began a relationship. During this period, Barbara experienced a great tragedy where she was shot by the Joker and confined to a wheel chair.

In a revealing moment in Nightwing Annual #2, we find out that after her accident, Dick visited Babs and the old flames heated up. When Barbara finds out that he was still with Starfire, she understandably became extremely angry. She was already emotionally vulnerable and Dick, while he may have had real feelings, took advantage of that. It is a moment that that we're sure Dick wishes he could have over again.

13 A LOVE BERMUDA TRIANGLE

13 dolphin triangle

Aquaman may be best known for his relationship with Mera, but he has been with some other ladies over the years. One of those was a naïve, peaceful young girl named Dolphin. She had been through some difficult trials, and eventually wound up working with Aquaman and Aqualad. Dolphin fell in love with Aquaman for a period of time, but something strange would follow. After some time, Mera would return from the Netherworld and Garth would return from a period of magic studies.

Eventually, Garth kissed Dolphin, and she experienced feelings that would blossom over time. Of course, Aquaman wasn’t exactly crazy about this at first. It isn’t often that Batman and Robin date the same girl, after all. But eventually, Aquaman found happiness with Mera and Garth would do the same with Dolphin. Sometimes it takes some crazy circumstances to find somebody to love.

12 BOMBSHELL BETRAYAL

12 bombshell

Following Infinite Crisis, DC titles jumped one year forward, and there were mysteries from that year that needed to be pieced together. During that time, the Teen Titans were a mess as they had gone through many members and the team was not the family it had once been. This opened a door for their foe Deathstroke to form his own team of Titans, called the Titans East.

Bombshell was a female character similar to Captain Atom who joined the team during the one year gap. She was quick tempered with a history of crime, but the team is surprised by her betrayal when she attacks her teammate Raven to get Deathstroke’s son Jericho, who had been downloaded to a disc. This was the thread that led the Titans to the discovery of the rest of the Titans East members, with whom they would eventually come into conflict.

11 ARSENAL BEDS A SUPER-VILLAIN

11 Roy Cheshire

As other entries on this list will bear out, Roy Harper isn’t exactly the best at making decisions. Green Arrow’s ward, who would evolve from Speedy to Arsenal and later Red Arrow, has a sordid history of poor life choices. One of those is his taste in women. During his time as an undercover government agent, Roy encountered Cheshire, a lethal but beautiful assassin. His job was to gain her trust and get her to turn over.

However, they did a lot more than turn over. They wound up falling for each other and eventually even having a child together. If there is a silver lining for Roy here, it would be that Lian, their daughter, would be a joy in his life for years to follow. He wound up raising her and while her life ends tragically later on, this relationship and its consequences would continue to plague him.

10 NIGHTWING COLLUDES WITH DEATHSTROKE

10 deals with deathstroke

The modern era of the Teen Titans is an ongoing saga with Deathstroke. It all began when Grant Wilson, Deathstroke’s son was hired to kill the Teen Titans. Grant’s use of a serum to make him have powers like his dad actually killed him. He was unable to fulfill his contract, leaving it for his dad to complete. However, Dick Grayson had done something none of his teammates knew.

It was revealed in the recent crossover, “The Lazarus Contract” that Deathstroke offered to stop hunting the Titans as long as Dick would help to teach his daughter Rose better values than her dear old dad. Dick was doing what was right for all involved, but his keeping it a secret from his friends for years, as well as the deal being with one of the Titans’ worst enemies, doesn’t exactly make you feel like trusting him again any time soon.

9 TIM DRAKE CLONES HIS BEST FRIEND

9 cloning conner

Losing one of your best friends at a young age is something nobody should have to experience. Unfortunately for Tim Drake, the third Robin, he had to deal with this following Infinite Crisis with the death of Conner Kent. Conner’s Superboy had come to lean on Tim as they dissected his identity, specifically who the other half of his DNA came from. He knew he was a clone of Superman and some human, and Tim helped him discover that human was none other than Lex Luthor.

They grew close as teammates and when Conner died, Tim felt lost. The team was in disarray, and Tim resorted to desperate measures. While there is a part of all of us that might understand using those means to bring your friend back, all it did was cause more pain for Tim and give him more pain.

8 RAVEN DISINTEGRATES A PRIEST

8 Raven wedding

When it comes to relationships, Dick Grayson has some interesting luck. On one hand, he gets be with some beautiful ladies, but on the other hand it seems that when things get serious, something crazy always happens. Some might say this is the life of a superhero. This happened when he made a pretty spontaneous decision to go through with marrying his longtime girlfriend, Starfire in New Titans #100.

Though there were some cold feet going in, things changed really fast when Raven, possessed by her demon father Trigon, disintegrated the priest out of nowhere during the ceremony’s most tender moments. Raven followed this up by planting one of Trigon’s seeds in Starfire. Needless to say, things weren’t quite the same for Dick and Kory following that wild turn of events.

7 SUPERBOY GOES LUTHOR

7 turning luthor

The Superboy known as Conner Kent’s struggle with his being a clone of both Superman and Lex Luthor plagued him throughout the Geoff Johns Teen Titans run of the ‘00s. It all came to head in Teen Titans #24 when Lex uses a keyword which flips a switch in Conner causing him to immediately shave his head bald and carve an “L” in his shirt over the Superman shield.

He went on to attack the entire team, including his then budding romantic partner, Wonder Girl. Not only that, but he also broke the arm of his best friend, Tim Drake. It was crushing to read at the time because Johns had done a remarkable job building Conner into such a likeable character who desperately wanted to be like Superman. Conner would recover, but it would take time for the emotional and physical wounds of this experience to heal.

6 DONNA VS. HER SON

6 Lord Chaos

What would happen if somebody from the future showed up and wanted to kill you because of the actions of your son in the future? This is the question that faced a pregnant Donna Troy in the early ‘90’s. She is told by the Team Titans that her son will become a villain known as Lord Chaos who will not only have the powers of a god, but go mad and kill his own mother.

This presented an incredibly difficult choice between her own powers or her son’s for Donna, but she chose to sacrifice her own. She comes to regret this decision and attempts to regain her powers. These events led to the end of her marriage, custody of her child, and her time as a Titan.

5 DEATHSTROKE STABS HIS SON

5 stabbing Jericho

Deathstroke has never been the model parent. Each of his children have had varying paths that have led them to many ugly places. For his son, Joseph Wilson, the Titan known as Jericho, it was a story that took some crazy turns. During the end of the ‘90s “Titans Hunt” story line, Deathstroke actually joined up with the Titans to help uncover the mystery of the Wildebeast Society.

They come to discover that a corrupted Jericho was the one behind the abduction of multiple Titans members. During the final battle, Jericho begged Deathstroke to kill him in a brief moment of clarity and, despite a lifetime of pain to follow, Deathstroke obliged. It was the end of a lifetime of bad choices by Deathstroke that remain his Achilles heel to this day.

4 ROBIN: KILLIN' LIKE A VILLAIN

4 Batman of tomorrow

One of the coolest stories of Geoff Johns’ Teen Titans run was called “The Future is Now” and included a look at a not so distant future for many characters from throughout Titans lore. For the core members of the team at that time, the future had brought a dramatic shift in a darker direction. The Tim Drake of this time was the leader of the team and he had become Batman. This was something the present day Tim we all knew did not think he would ever care to do.

Not only that, but Tim’s dark turn included his use of a gun and lethal force in taking down the rogues gallery we all know so well. In fact, what was once Arkham Asylum had become a cemetery for fallen comrades and slain villains. This all successfully scared the team into taking steps to change the future.

3 HANK HALL: EXTANT

3 Hank Hall Extant

Hank Hall is most often remembered as Hawk, the “chaos” to Dove’s “order” in the duo that often served as members of the Teen Titans. During a later story called Armageddon 2001, he was revealed to become something far worse in the coming years. It was revealed that the he would become an evil world conqueror known as Monarch. This was horrific not just because of the evil that Hawk would become, but because it was actually not the original plans of the writers of the story.

Hawk was chosen as a replacement for the leaked identity of Captain Atom as Monarch. The path continued for Hawk as he would then channel his powers into a more powerful force known as Extant, who was the right-hand madman for Parallax during Zero Hour. It took years of fan complaints and clever storytelling to restore Hawk’s positive legacy.

2 SPEEDY SHOOTS (UP)

2 Roy's drug use

In terms of comic books and pop culture, the Speedy drug usage stories in Green Lantern/ Green Arrow are some of the most well-known. In the early ‘70s this kind of blunt storytelling that went right at the heart of real world issues was not common. Roy’s addiction to heroin was serious for the character and the reader felt it.

What may have been just as bad as Roy’s initial decision to start using drugs was Green Arrow’s reaction of throwing him out on the streets. Had it not been for Hal Jordan’s placement of Roy under Black Canary’s care, Roy’s life may have continued to spiral out of control. He still carries an addictive personality in a lot of modern stories. Hopefully, Roy will continue to learn from his past mistakes and not let himself succumb to some of his past vices.

1 TERRA & DEATHSTROKE

terra

This was and still is the most iconic story in Teen Titans history. It still makes fans shudder to think of a 15 year old girl not only working for Deathstroke, but also having a physical relationship with him as well. This was uncomfortable for readers to swallow as Terra had been working with the team for a while before “The Judas Contract” story brought this all to light. But as readers, we struggled with the whole situation as a normal human reaction.

Her infiltration of the team and the data it gave Deathstroke to help fulfill his contract on the team is heartbreaking because of the pain of characters like Beast Boy, who had developed feelings for her and wanted to save her despite it being too far gone. It remains a perfect example of risk-taking storytelling that paid off big time.

What other regrettable moment can you recall in Titans history?  Let us know what you think in the comments.