For a webcomic that focuses heavily on adult humor and gaming and nerd culture, ''PennyArcade'' does have its moments of sadness.
* The last panel of [[http://www.penny-arcade.com/comic/2006/08/28/ the conclusion to Armadeaddon]].
** To explain: The guy standing with Gabe and Tycho in the photo is Jim, an old friend of theirs. Jim came back as a skeleton in the story arc, so Tycho is remembering all the good times they had with him back when he was alive.
* [[http://www.penny-arcade.com/comic/2014/11/14/a-ring-and-a-prayer "A Ring and a Prayer"]], when a despairing [[SonicTheHedgehog Sonic]] (in his SonicBoom garb) begs Gabe, who is in tears, to shoot him at point blank range in the head if he really loves him. He complies.
-->Sonic: "Do it. If you ever loved me, you'll do it."
** [[HarsherInHindsight It's even more gut wrenching]] in light of SonicBoom: Rise of Lyric becoming a critical and commercial flop.
* The [[http://www.penny-arcade.com/comic/2009/04/10/ end]] of the "Seventh Spring" arc.
* When you realize what happens to the two of them, [[http://www.penny-arcade.com/comic/2008/07/04/ this]] strip turns on the waterworks.
* Some of Tycho's words after the birth of his daughter are tearjerking and heartwarming at the same time.
-->"I need you to be thus armed because I fear your mother and I have played a trick on you; we have brought you to a place where [[SlidingScaleOfIdealismVsCynicism hidden weaponry is sometimes necessary]]. In our defense, and I recognize that it may be insufficient, this was the only world available to us."
* [[http://penny-arcade.com/comic/2005/02/21 Part 1 of the story arc Ripped From Today's Headlines]], the last panel is pretty heartwrenching. Tycho holding his dead wife in his arms, realizing that he just killed her, [[MyGodWhatHaveIDone and feeling really bad for it]].
--> '''Tycho''': Oh my god. Oh my god. Please don't leave me.
* [[http://penny-arcade.com/2012/08/01/nathan This news post.]]
* [[http://www.penny-arcade.com/comic/2005/09/07 Anti-anxiety medicine.]] Half TearJerker, half NightmareFuel.
* Gabe [[http://penny-arcade.com/comic/2012/11/30 teaching his son about Online Safety]] can really hit home to any parent watching their kid grow up.
* [[http://www.penny-arcade.com/comic/2013/06/24 This]] strip (and the post for it) from Tycho on playing VideoGame/TheLastOfUs. Talk about [[AdultFear Adult Fear]].
* Tycho's 10/09/13 news post, full stop. In essence, he's talking about his father and the divded relationship with him. On one hand, he has always been used as an example of how not to be and on the other hand how he helped form Tycho's love of games and his current life in general. Then we reach the final paragraph; "I was angry at him for twenty years, but I canít be mad at the bent up shape on this bed. He isnít the right size; he looks like a boy. I tower over him and it is hard to understand how that could ever be. There is a button he can push when it hurts him, and he is always pushing it."
** [[http://penny-arcade.com/news/post/2014/08/01/further-intrusions-of-actual-life It got worse. Much worse.]] A little less than a year later, Tycho's father finally passed away, after a long, horribly painful fight against a virtually incurable cancer type. Tycho's description of his father as a withered, tortured mass of flesh is both tear jerking, and borders on NightmareFuel. On top of all this, now Tycho's own son now requires medical aid due to an unspecified chronic disease, and its clear that the author nears the end of his rope. Things are not looking good.