Born in Dublin and educated at Belvedere College and the Metropolitan School of Art, Whelan was a student of William Orpen. He first exhibited at the Royal Hibernian Academy in 1911, and was awarded the Taylor Art Scholarship five years later in 1916. He exhibited nearly 250 works at the RHA from 1911 until 1956. He painted many portraits of Irish Republican Army volunteers, including General Richard Mulcahy and Michael Collins. He was the designer of the first Free State commemorative stamp, issued in 1929 for the Centenary of Catholic Emancipation, a portrait of Daniel O'Connell. One of his closest friends was tenor John McCormack, who unsuccessfully tried to persuade Whelan to move to the United States.
- Snoddy, Theo. Dictionary of Irish Artists: 20th Century, 2nd Edition. Merlin Publishing, Dublin, Ireland, 2002. Pg.703-05. Retrieved Apr. 02, 2008.
- "Archived copy". Archived from the original on 2008-02-14. Retrieved 2008-03-12.CS1 maint: Archived copy as title (link) Leo Whelan at the Crawford Art Gallery. Retrieved Mar. 11, 2008.
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