The oldest artist I can find (who’s still alive) is Ray Anthony, who had a #7 hit in 1953 and is now 102. The oldest overall that comes to mind is Vera Lynn (103). Can anybody else find any artists who lived longer?

Not juat a charting artist, but a charttopper, Sally Sweetland reached 103 years 4 months 2 weeks, which edges ahead of Dame Vera Lynn's 103 years 3 months, and must make Sally the longest lived charttopping artist, if not the longest lived charting artist.

This thread might help you, a list of the earliest-charting artists who reached top 20 and are still alive: http://www.buzzjack.com/forums/index.php?showtopic=269554