Name a band and I've most likely seen them live.
What era's though... for example, have you seen The Doors/Hendrix, and if so, have you seen the modern bands like Kings of Leon?
I'm a lot younger than you and Maris, so I'd imagine ya'll have seen 10x the amount of music I've seen, but for the amount of shows I've been to, I think I've still got a pretty good resume, and it's hard to think of all of them off the top of my head without missing a lot of good ones. I'll try to break them down into categories, but I'll still be leaving out a lot.
One of the great things about this era of music is that there seems to be more festivals than ever before. I grew up not too far from Bonnaroo, so I was always there, and went to the original Rothbury, went to most Voodoo's, went to most NO Jazz Fest's, and went to most Memphis in May's. That's allowed me to see the spectrum of great artists from the 60's (but in their present states) as well as the great (and up-and-coming) artists of the present.
Like I said, I'll probably leave a lot out, but here's an attempt (in no particular order) -
Alternative: Red Hot Chili Peppers, Pearl Jam, Rage Against the Machine, Jane's Addiction, Smashing Pumpkins, Stone Temple Pilots, 311, Nine Inch Nails, Flaming Lips (three times), Butthole Surfers, Modest Mouse, Blues Traveler, Primus (and another time I saw the Flying Frog Brigade), Weezer, Mars Volta, Phoenix, Dave Matthews Band (a few times, unfortunately), TV on the Radio, the XX, the Black Keys, REM (they sucked, as expected, so I left half-way through to see Trombone Shorty), etc.
Hip-hop: Nas, Jay-Z (twice), Eminem, Lil Wayne (three times), Snoop Dogg, Juvenile, Three Six Mafia, Jay Electronica (got on stage), The Roots (twice), Kid Cudi, B.O.B. (Kid Cudi sucked, and B.O.B. was on afterwards and did his set til the sun came up to make up for it), Wale, Yo Gotti and a lot more local rappers, etc.
Electronic: Justice, Tiesto, Deadmau5 (twice), Ghostland Observatory (twice), Passion Pit, Kraak en Smaak, Bassnectar (several times), LCD Soundsystem, Pretty Lights, Girl Talk (unfortunately), Disco Biscuits (several times), etc.
Jam: not the original Grateful Dead but Phil Lesh and Friends, Mickey Hart Band, and Bob Weir and Rat Dog, Widespread Panic (several times), Gov't Mule (several times), not the original Allman's but saw Gregg at the House of Blues, not Phish but saw Trey Anastasio (and literally fell asleep on the hill during it) and Mike Gordon (the bassist) do solo acts, Lotus, Galactic (several times), Keller Williams, not the original String Cheese but EOTO, and all that stuff like Umphrey's, Tea Leaf Green, Michael Franti, etc.
Reggae: Jimmy Cliff, the Wailers, Damian Marley, Collie Buddz (a few times), etc.
Southern Rock: John Fogerty, Lynyrd Skynyrd (twice, but both bastardized versions of the original), Kings of Leon (several times before they went mainstream and a few after), Zac Brown Band, Drive-By-Truckers, etc.
Misc: Stevie Wonder, Bob Dylan, B.B. King (several times), Steve Vai, Jeff Beck, Blondie, Jello Biafra, Jimmy Buffet, Robert Randolph, Steve Martin and the Steep Canyon Rangers, etc.
I could probably add a lot more bands to that list, but those were just the ones that came off the top of my head. If you want to know how any of them were live, lemme know, because most of those guys are still touring.