Ehhh, dated references are kind of a weird thing for me. I actually like them; they sort of contribute to the setting of the song. When lyrics bring up what was relevant during the time they were written, they help establish a spot on the historical timeline, allowing you to know what was going on back then.
I remember some historian discussing in an article about how hip-hop is one of the greatest modern assets to historical studies due to the dense, plentiful lyrics that reference every little thing about culture and society at the time of the music's creation. Eminem jokingly dissing Fred Durst, Brittney Spears, and other artists may be corny to some, but it gives the future listeners a broader perspective of the music industry of the time. His mentions of Columbine, defending Marilyn Manson, and his battles with the conservative media frame a picture of the current events and controversies of the day.
To me, it is an asset. Even going back and listening to Busy Bee ask the crowd what their favorite brand of jeans are, and then hearing a packed house yell out different shit...that's dope to me. It educates me that that sort of shit was more culturally important back then.