From Homestar Runner Wiki
Penny Arcade is a web comic about video games that stars Tycho and Gabe, the alter egos of creators Mike Krahulik and Jerry Holkins respectively. They also hold a convention called PAX, the Penny Arcade Expo. Tycho was able to appear with Strong Bad and other video game characters due to the episodic video game Penny Arcade Adventures. Although the comic has been referred to in the past, most references to Penny Arcade and PAX are due to Telltale Games' involvement in Strong Bad's Cool Game for Attractive People and Poker Night at the Inventory.
Tycho first appeared with Homestar Runner characters in Make a Scene With Telltale at PAX 2010 when he was a suspect along with Marzipan in a murder. However, in that cartoon, the characters had dialogue and voices written and performed by fans at the Penny Arcade Expo. The first instance of characters from both universes interacting together with dialog written by the license holders came in Poker Night at the Inventory when Max and Strong Bad were both participants in a poker tournament at an exclusive club called The Inventory where video game characters relax on their days off. All of the characters in the game were performed by their official voice actors, including Strong Bad. Tycho was voiced for the first time in the game.
 Tycho's relationship with Strong Bad
While most of the players at The Inventory's poker game seem casually friendly towards each other, Strong Bad and Tycho have a barely concealed hatred of each other. Strong Bad thinks Tycho is a dork and mocks penny-arcade.com calling it a "Geocities site". In response, Tycho calls him a "chuwero", a made up racial slur.
- Make a Scene with Telltale at PAX 2010 — Tycho is in the toon along with Marzipan and Strong Sad. The characters are voiced by audience members.
- Poker Night at the Inventory — Tycho is one of the players, along with Strong Bad. Strong Bad makes fun of PAX again, as well as the Penny Arcade web comic and Tycho himself.
- Email web comics — The art style and premise of the "GAMERJōX" web comic is based on Penny Arcade with Strong Bad resembling Gabe.
- Make a Scene with Telltale: Strong Bad Edition — The "Make a Scene" takes place at PAX, and Strong Bad and The King of Town (as voiced by an audience member) make fun of the expo.