PaRappa the Rapper Contest
The PaRappa the Rapper contest was a competition held by Sony Computer Entertainment America (SCEA) in 2007 which Chris entered in order to win a PSP for his sweetheart Megan Schroeder, the prize also included a trip for two to Seattle, Washington to receive the PSP which he hoped to take Megan on, ultimately to share a hotel room with her and woe her into having sex with him for the first time.
Chris also badgered his half-brother Cole Smithey to vote for him in return for him finding out information from his mother whom Cole's biological father was. Chris' wasn't interested in Cole's plight, and in return Cole never voted for him.
The competition was eventually won by Adam Stackhouse, whom Chris bares a grudge against for winning as he felt Adam had cheated in order to win the contest.
Chris' Video Entry to the Competition
See Also
GameStop Guitar Hero Contest - A Similar competition Chris entered (and won) a year later.