Stadium shows and huge outdoor venues always seemed to me to be more about the fact that thousands of people got together in one place and jumped up and down in time, more or less, to the music, drank copious amounts of alcoholic beverages, smoked weed, and got crazy. The events create great memories (in most cases) but the music is almost secondary. The best live shows I've experienced have been in venues where the sound is great, the audience attentive and the artist communicates with listeners.
My favorites:
Merle Haggard in City Auditorium, Austin, TX in 1981 or thereabouts. Merle's band, mostly Nashville players, played everything from hardcore country to jazz and his voice was at its peak.
Leon Rausch and the Original Texas Playboys, intersection of 6th and Congress Ave., Austin, TX, early 80s. KLRU, the Public TV station who does Austin City Limits, arranged this concert for a Bob Wills tribute to air on Austin City Limits. It was memorable for the fact that the players, at one time or another, had all played in the band with Bob Wills. Classic western swing by the guys who helped invent it.
Ray Charles in the Paramount Theater, Austin, TX, mid-80s. I managed to see Ray in venues ranging from high school gyms to modern big-city rodeo arenas. His band was always great, his backup singers soulful, and Ray always delivered, but in a smaller venue up close, what an experience.
Lyle Lovett and his Big Band, Majestic Theater, San Antonio, TX, 2004. Lyle's writing and arrangements are so good it makes you cry, and when his gospel songs are delivered backed by a Nashville choir, you'll convert. His shows are so classy it's scary. I've seen Lyle several times, always in venues like the Majestic and Austin's Paramount. His country band is great as well, but I really love his Big Band shows. What a great artist.
Delbert McClinton, Gruene Hall, New Braunfels, TX, multiple times in the past 3 years. Delbert gets better with time, and his players are top notch. His shows always get you up and moving. The ambience in Gruene Hall takes you back 60 years and adds grit to his shows. Great R & B and blues, with a sound that will never get old.
Taj Mahal, Gruene Hall, with Mike Finnegan on Hammond B3, and the rest of the Phantom Blues Band. Finnegan plays like crazy and nearly matches Taj's vocal blues sound.
Aaron Neville, with brother Charles on sax, and a quartet, 2004, Laurie Auditorium, Trinity Univ, San Antonio, TX. Always great players and listening to his voice is an awe inspiring experience. How does he do that?
Wynton Marsalis and the Lincoln Center Jazz Orchestra, Laurie Auditorium, 2004. The sound is so good and the audience so rapt, that artists can't help but deliver great performances. These guys are the best.
Sorry for the long post. I love good music, played live, and there is so much good music out there. If you find the right venue and the right artists, it's a transcendent experience.