When he asks why Homer would be so selfish in doing so since Marge promised to put that in a trust fund for his future, he explains that he needed the money.
Homer had to buy back incriminating photos of himself endangering Bart's life from a hotel balcony to avoid a scandal.
He befriends Hawk and decorates his loft with luxuries, and when the rest of the family visit him, Bart prefers his new life and still refuses to come back.
Homer starts to earn back Bart's money by acting in an advertisement for an impotency drug and which he's embarrassed of.
This was referenced in this episode during a joke where Lisa tallies the number of Homer's schemes at 300; Marge comments "I could've sworn it was 302."
[4] In 2007, Simon Crerar of The Times listed Tony Hawk's performance as one of the thirty-three funniest cameos in the history of the show.
[5] In 2011, Colin Jacobson of DVD Movie Guide said the episode seems dated due to the appearance of Blink-182 and Tony Hawk, who were popular in the early 2000s.
"[6] On Four Finger Discount, Guy Davis and Brendan Dando also thought the guest stars were reflective of the early 2000s.