It must be tough to be Martha Wainwright. Her father Loudon Wainwright III has been compared to Bob Dylan. And her singer-songwriter brother Rufus has 7 albums (not to mention that tear-jerker scene in Shrek), plus, he counts Elton John among his biggest fans. As Martha told Rolling Stone, being part of a musical dynasty means “the bar is really fucking high.”

Unlike her Wainwright kin, Martha took a winding route to music, first studying drama in defiance of the family pedigree. Then music crept back into her mind, first leading to a DIY cassette-only release, followed by some stunning EPs, guest vocal appearances on family recordings, and eventually a self-titled debut album in 2005. Collaborations since have included work with Snow Patrol, and a guest appearance by Pete Townshend on her second album.

Now that she’s hitting the road to promote her third album, Come Home to Mama, Chicago looks back at some of Martha’s memorable, strange moments.

  • Martha’s intense emotional rawness in Proserpina is a little unnerving. It was the last song written by her mom, the late folk singer Kate McGarrigle. In the video, the camera stares Martha’s wailing face, putting us right in the middle of a haunting dialogue between mother and child.
  • In 2005, Martha released an EP, Bloody Mother Fucking Asshole, right before her full-length debut. The charming title is a direct nod to her father Loudon. She often mentions him at her shows, before thrashing angry chords on her guitar and telling of a painful childhood.
  • In 2009, she decided to make an entire live album of Édith Piaf covers, honoring her long-time obsession with the legendary French singer.
  • In Come Home to Mama, she inches further away from a traditional style. We hear more experimentation across the board—chord progressions are less predictable, instruments are less acoustic, and her voice is performing more acrobatic feats. Her melodies quickly alternate between the grounded movements of older folk tunes and wild runs—these sound like younger vocal innovators like St. Vincent and The Dirty Projectors.

Her style has the raw ingredients for something groundbreaking. If the intriguing presence in “Four Black Sheep” or the psychedelic lounge vibe in “Some People” are glimmers of her future works, then Wainwright has plenty of fantastic weirdness to come.

Martha Wainwright plays at City Winery (1200 W. Randolph) at 8 p.m. on Sunday March 24. $20.