Belle and Sebastian released their debut studio album Tigermilk in mid-1996 on local label Electric Honey.

By July 1996, the band received praise by radio DJs, and by August 1996, they got attention from interested record labels.

[12] Author Dave Thompson, in his book Alternative Rock (2000), described the album's sound as: "Blessed with vocals straight out of Donovan's '60s, and a musical echo of vintage Boomtown Rats, topped off by a West coast vibe tinged with unbridled Scots romanticism".

It was issued in the United States in early 1997; the decision to do this delayed the follow-up, with the band instead opting to release three EPs, Dog on Wheels, Lazy Line Painter Jane and 3.. 6.. 9 Seconds of Light (all 1997).

The EPs were successively climbing the charts in the UK while If You're Feeling Sinister was gaining traction at American colleges.

[28] If You're Feeling Sinister also appears as an entry in the book 1001 Albums You Must Hear Before You Die as chosen by music critics.

[32] Reflecting on it 20 years on, Stereogum's Tom Breihan claimed that Sinister could be "too influential", despite it taking "a long time for [the band's] influence to spread."

[33] Other groups that critics have noted Sinister inspiring include Alvvays, Hovvdy, Kings of Convenience, and the Shins.