Having come up in the early 2000s with the Polyphonic Spree, St. Vincent — now age 35 — would seem long in the tooth for a pop star. However, the one-time member of Sufjan Stevens’s touring band has reinvented herself more than once, going from soft jazz rock on her 2007 debut album Marry Me to an experimental collaboration with former Talking Head David Byrne, Love This Giant, to the alt-rock heroine whose self-titled fourth solo album won her a Best Alternative Album Grammy, the first female solo act to win that category for the past 20 years. Her newest full-length, Masseducation, drops this month in advance of her January 27 appearance at Observatory North Park. Two singles have been released so far for the album, which she recently told Pitchfork is “all about sex and drugs and sadness.”