I believe Earle's last appearance was
on Sept. 19, 2006, as Tom's neighbor and High Priest of the Church of Satan, Keith Kincaid. Bryce's call the next week with details on the COS's Fun Faire is indispensable. Dennis Lindsey, Tom's other neighbor, who called and gave Tom a hard time about his Halloween setup. You can hear him on the October 24, 2006 show.
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Jon Benjamin did a lot of interviews as various characters early on. My personal favs are April 3 and 10, 2001, as
Tonight Show producer Brad Lester (a great slow burn that really really pays off at the end) and Feb. 13, 2001, as Ron Garver, author of
Upright Positions: Flying the Erotic Skies (which is hilarious throughout). May 21, 2002, to me, is classic Best Show, with Tom playing it totally straight while Horatio Sanz and Jon Benjamin frustrate Matt Walsh.
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Check out
this interview with S&W on AST Radio by isos and our own Jouster, which addresses the "What happened to Andrew?" portion of your question.