The afternoon before the Wailin’ Jennys were scheduled for their Chicago debut, opening for Loudon Wainwright III at the Old Town School of Folk Music, their old friend serendipity dealt them another card The Wailin’ Jennys Serendipity Sings by Michael Parrish The afternoon before the Wailin’ Jennys were scheduled for their Chicago debut, opening for Loudon Wainwright III at the Old Town School of Folk Music, their old friend serendipity dealt them another card. The trio arrived in Chicago to the news that Wainwright was trapped by a cancelled flight in Winnipeg, which ironically is home base for two of the three members of the Jennys ǃ