Years: 1927-1928
How Drake feels: “Uh, when did you get like this?/Least you coulda done is gone an give me a warning/I don't regret like this” (“Let's Call It Off”)

Why mess up a good thing? In the Tigers' inaugural season, they tried implementing a silhouette of a tiger which lasted all of one season. After a little more than 20 years of refining their iconic “D” logo, they made the terrible decision of venturing back into creating a tiger logo and this Microsoft Paint-like rendition was dreadful. Just look at the damn thing! Ugh! Not surprisingly, the MS Paint Tiger lasted one year and went right back to a revised version of their former logo.