While the Jojo's Bizarre Adventure series has become famed for its musical references, the series has referenced media other than pop and rock music, and its weirdest reference is a cameo hidden in one of the franchise's darkest scenes.
Jojo's Bizarre Adventure's third entry, Stardust Crusaders, is perhaps the most popular, featuring both the spirit-beings known as Stands that the series would ultimately be known for, as well as the return of its first and best-known villain, DIO. The climax of Stardust Crusaders is set in Cairo, Egypt of 1989, and while the final battle initially begins in DIO's mansion, the conflict soon spills out into the streets, dragging in many innocent passersby who can't even understand the nature of the battle going on around them.
In chapter 138 of Stardust Crusaders, also referred to as chapter 251 of the series overall, night time falls, and DIO takes to the streets, no longer restricted by his vampiric weakness to sunlight. Not knowing how to drive a car, DIO hijacks a limousine containing a US Senator and forces him to drive. The Senator rapidly loses his mind when subjected to DIO's supernatural abilities, and when DIO urges him to drive through a crowd of people on the sidewalk to bypass traffic, he does so with glee, sending people flying and coating the car in blood. One victim of DIO's rampage is, shockingly, Waldo/Wally of Where's Waldo? fame, whose striped body can be seen flailing in the air as he stares directly out of the panel at the reader. His identity was made clearer in the colorized manga, where he retains his usual red and white striped color scheme.
As a British children's character, Waldo certainly seems a strange choice of cameo, but the character was at the peak of his popularity in 1992 when the chapter was first released. In fact, the issue of Weekly Shonen Jump that this chapter was released in featured a "Where's the Jump Hero?" Quiz, a Waldo-style puzzle featuring Shonen Jump characters of the time (including Jotaro). The intent seems to have been a dark joke referencing the issue's theme, as Waldo is often hidden amongst crowds of people in his home series. Unfortunately, the car scene was considered so violent it was omitted from the anime adaptation, likely due to real-world incidents of vehicular terrorism that brought the scene a bit too close to reality. As a result, Waldo's cameo is excluded from the anime altogether, although the anime version of the sequence still shows the car covered in blood later.
Given his love for inserting references into his work, it should come as no surprise that Hirohiko Araki has had some strange ones over the years, but Waldo and the context of his appearance has to be one of the strangest that Jojo's Bizarre Adventure has ever seen.