Funny Aneurysm Moment: The story of his bitter divorce (and how horrible his wife really was, considering that she tried to kill him, stole his money, cheated on him, and lied to the judge stating that Titus was abusive) in Love is Evol makes parts of his earlier specials (and the sitcom Titus, which aired around the time that Titus was married to Erin Carden), where he praises his wife and says that she's better than his first girlfriend (the Jewish girl who, much like his mom, was beautiful, sexy, highly-intelligent, and mentally deranged), very hard to listen to.
On the second Christmas episode of Titus called "Houseboat," one of the Neutral Space cutaways shows Titus holding a ticking present and happily declaring that his father finally knows how to feel love and forgiveness instead of hate and vengeance, adding that next year, Titus will teach his dad that "heart attacks are not like women; you just can't keep having them." Titus's dad actually did die of a heart attack (while driving a sports car that Titus gave him during a ski trip), according to The 5th Annual End of the World Tour.
The Woobie: Considering everything that's happened to him (living with his Jerkass dad, having a mentally ill mom who committed suicide, having his sister commit suicide after dating a guy who kept breaking up with her, getting abused by his first girlfriend and his ex-wife, and nearly losing everything in a divorce), this troper can't be the only one who wants to give Titus a hug, right?
Iron Woobie: Considering he hasn't just gone off on a rampage yet (or killed himself like his mom and sister did -- in Neverlution, he mentions that he should be the only person in the world legally allowed to take antidepressants because of everything that's happened to him in his life, but he doesn't need it because he takes his outrageous and shocking life stories and turns them into comedy for others, making himself an antidepressant), I think he qualifies for this as well.