OK, I know that the original question was what modern covers (from 1990 on) would the boys have done, but I'd like to have a little fun with this. I hope you all will indulge me. Turns out this is something I have thought about since my first show in 1978. I wasn't all that familiar with their music, but I was very impressed, and when they did "Good Lovin'" and I heard what they did with it I was hooked for life. So here are a bunch of songs that I have said to myself "Wow, imagine the Dead doing that. Imagine Jerry steppin' up to the mike to sing this line!" I know that some of these are pretty odd picks - but indulge me! Thanks.
*It Don't Mean a Thing If It Ain't Got That Swing (Duke Ellington) - Jerry
*Great Balls of Fire (Jerry Lee Lewis) - Jerry or Bob
*And When I Die (Laura Nyro, as performed by Blood, Sweat and Tears) - ??
*Rock the Boat (Hues Corporation) - imagine Jerry & Bob stepping up to the mic sinnging "Our love is like a ship on the ocean, we've been sailin' with a cargo full of love and devotion"
*That's Life (ala Sinatra) - Jerry
*Satisfy My Soul (marley)
*Let It Roll (Little Feat)
*The Shape I'm In & Don't Do It (The Band) - I also agree with Ophelia which was already mentioned
*Spirit in the Sky (?? - a real oldie)
*Ball of Confusion (with additional new lyrics relevant to more current events from Hunter)
*Ding Dong the Witch Is Dead (Bob) --> If I Only Had A Brain (Jerry!!!!!!) --> GDTRFB --> Follow the Yellow Brick Road (instrumental)
*Sentimental Journey (Green, Brown and Homer)
*Anything by Robert Johnson, but esp. If I Had Possession Over Judgement Day, Love In Vain, Ramblin' On My Mind, and Terraplane Blues
*Moon River (Henry Mancini and Johnny Mercer, from Breakfast at Tiffany's) - Bob
*Sing, Sing, Sing (With a Swing) - or another Benny Goodman instrumental like One O'Clock Jump or Stompin' at the Savoy
I know I am weird, but Jerry's voice and guitar still ring true for me and I hear it everywhere. God I miss him.