While you could argue that the first Wiretap episode ever was “Buddy Picture” with Josh Karpati on This American Life (maybe more like a pilot, given that Josh’s voice is much less shrill in this), according to CBC, “It’s Over” was the first:
Saturday, on the premiere episode of Wire Tap with Jonathan Goldstein, the heartbreak of breaking up and the delicate hope of new beginnings. Devastatingly intimate phone calls. How can you not listen in? That’s Wire Tap, Saturday morning at 11:30 (noon NT) on CBC Radio One.
In this episode, we hear Melissa Kent, Starlee Kine, Howard Chackowciz, Burt Covit, James Hurst and Juliette Water(s?). Tonsofun. Anyway, I’ve written a summary here.