The Grateful Dead have always been my favourite band to see live. I've seen them roughly 150 times.
On the other hand, when I want to kick back and listen to studio albums, The Rolling Stones have always been my favourite.
In my opinion, The Dead went downhill after Brent died, late 1990. If you're exploring The Grateful Dead for the first time, stay away from the live shows from sept90-95.
I stopped going because the mix was bad and Jerry was exhausted. I gave away about 50 DVD's i had from this period, it was too painful to watch.
Blues For Allah is my favourite album.
The beauty of their live shows was, the constant changing of the setlist...if you saw 10 shows in a row, you would see a wide variety of songs.
Here's a sample from June of 83 (you really can pick any month any year)
06-18-83 Saratoga Performing Arts Center, Saratoga, N.Y. (Sat)
1: Bertha> Jack Straw, Bird Song, Mexicali> Big River, Althea, Bucket> Deal
2: Scarlet> Fire, Playin> Drumz> Wheel> Playin> Morning Dew, Throwing Stones> NFA> Touch E: Don't Ease> Saturday Night
06-20-83 Merriweather Post Pavilion, Columbia, Md. (Mon)
1: Minglewood, TLEO, Rooster, Peggy-O, Esau, Tennessee Jed, Bucket, West L. A., Music
2: China Cat> I Know You Rider, Samson, He's Gone> Truckin> Drumz> Bob Star> Other One> Wharf Rat> Sugar Magnolia E: Baby Blue
06-21-83 Merriweather Post Pavilion, Columbia, Md. (Tue)
1: Alabama> Greatest, Dire Wolf, Me & My Uncle> Cumberland, Cassidy, Big RxR Blues, All Over Now, Loser, L. L. Rain> Might As Well
2: Touch> Woman Smarter, Terrapin> Estimated> Eyes> Drumz> Throwing Stones> Black Peter> Around> Good Lovin E: U. S. Blues
06-22-83 City Island, Harrisburg, Pa. (Wed)
1: Stranger, FOTD, C. C. Rider, Ramble On, Esau> Deal
2: Bucket, China Cat> I Know You Rider> Playin> Drumz> Spanish Jam> Miracle> Stella Blue> GDTRFB> NFA E: Brokedown
06-24-83 Dane County Coliseum, Madison, Wi. (Fri)
1: Shakedown, Far From Me, Candyman> Rooster, B. E. Women, Mama Tried> Mexicali, Althea, Bucket> Deal
2: Help> Slipknot> Franklin's> Sailor> Saint> Drumz> Truckin> Morning Dew> Around> Johnny B. Goode E: Don't Ease
06-25-83 St. Paul Civic Center Arena, St. Paul, Mn. (Sat)
1: Jack Straw, TLEO, Cassidy, West L. A., Esau, Big RxR Blues, Lazy Lightning> Supplication> Might As Well
2: Touch> Samson, Ship Of Fools, Woman Smarter, Uncle John> Drumz> Throwing Stones> Black Peter> GDTRFB> Saturday Night E: Baby Blue
06-27-83 Poplar Creek Music Theatre, Hoffman Estates, Il. (Mon)
1: Bertha> Promised, Dupree's, Minglewood, Bird Song, Me & My Uncle> Mexicali, Cold Rain> Bucket> Sugaree
2: Scarlet> Fire> Estimated> Truckin> Drumz> Other One> Wheel> Good Lovin E: U. S. Blues
06-28-83 Poplar Creek Music Theatre, Hoffman Estates, Il. (Tue)
1: Stranger, Dire Wolf, All Over Now, B. E. Women, Rooster, Tennessee Jed, L. L. Rain> Deal
2: Help> Slipknot> Franklin's> Woman Smarter, He's Gone> Drumz> Throwing Stones> NFA> Stella Blue> Sugar Magnolia E: Iko Iko