For Cheshire Smile, Sanford Biggers references the infamous cat from Lewis Carroll's Alice in Wonderland, who disappears after sharing riddles or koans (Buddhist paradoxes), leaving behind only his bodiless, floating grin. Moving beyond the simple representation of the floating smile of the Chesire cat, Biggers uses the image as a reference to the “raced” body and the complex fact that some black performers from early minstrel shows through current hip-hop have embraced and exploited racial stereotypes as a means for social and financial ascension. Working with these themes, Biggers created this piece which features the light-up smile of the Chesire cat against a plain black background.