Big Rigs is a good choice, although it's kind of spot on in that it's notoriously awful, and it's awfulness is apparent straight from the onset, and it might be enjoyed in a "so awful it's hilarious" way.
Everyone knows my feelings on Ultima IX. You could try and trick him into thinking it was acclaimed, but that ruse wouldn't hold up long. Can't really be enjoyed even on an ironic level, so it might be a good candidate for punishing your friend.
It's kind of hard to find a more modern offering that gives that level of suck. Most of the worst offenders these days are aggressively mediocre and uninspired, rather than hilariously broken and offensively terrible.