Gary "DICKS" Oak is Professor Oak's grandson who appears in Super Pokeman 64 bloopers: WELCOME TO POKEMANS! and Super pokeman 64 bloopers: GYMS AND BADGES. He ends up being Mario's nemesis throughout the blooper. People don't think about him much and sometimes thinks that he's a girl.
Gary's Groudon, who he calls "MLGsexy wife" was the first Pokemon he sent out in the Pokeman 64 series, where he challenged Mario to a fight, MLGsexy wife was unfortunately killed when Mario immediately shot him with a pistol, he had not been seen again since. Likely meaning that he died of the gunshot.
Gary's Weedle is the Pokemon he sent out when he fought Mario a second time, it is apparently a lot stronger than it looks, as it was able to send Toad flying in one blow. Weedle, along with Dicks, were sent flying when Luigi Mega Evolved into Weegee. Like Groudon, he has not been seen since.