When You're Smiling is an American popular song written in 1928.

When You're Smiling may also refer to:

• When You're Smiling (film), a 1950 musical film by Joseph Santley
• When You're Smiling (Bradley Walsh album), 2017
• When You're Smiling (Regis Philbin album), 2004
• "When You're Smiling and Astride Me", a song by American folk musician Josh Tillman

This disambiguation page lists articles associated with the title When You're Smiling.
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