I think the mashup could have been pulled off better.
For example, "Chicken and Waffles with Maple Syrup" is quite popular. We even have a restaurant here in San Francisco where that is their signature dish.
Here's one set of possible substitutions and accompanying beverage ideas which might work.
1) I'd say that if the whipped cream were made "savory" with somethng salty like bacon or ham bits, bacon drippings, and a little black pepper, it might pass as a kind of "red eye gravy" styled whipped cream.
2) The chocolate sauce would have to be done totally dark chocolate (70% cacao or above) savory and might work as perhaps a kind of Mexican mole with smoked chipotle..
3) Substitute the marichino cherries for small, marinated or pickled "cherry tomatos" and/or small, marinated red peppers, and perhaps that might work.
4) Not sure what sauce is under the piece of chicken, but again anything sweet will probably not work with the substitutions described above. I'd put it on a bed of smooth polenta (rather than fluffy) to counter the dryness of the batter and balance with the other substitutions above.
The best drink option would probably be a Negro Modelo or an IPA beer. If you must go with wine, a young Sauvignon Blanc as a white, or either a Syrah or Zinfandel might work as a red. An unsweetened hot "Almond Horchata Coffee with Tequila" styled drink might also work with the sundae.
With what I have described, would anybody eat the modified sundae?