"I Pity the Fool" is a soul blues song originally recorded by Bobby Bland in 1961 for his first Duke Records album, Two Steps from the Blues. Many music writers believe it was written by Joe Medwick, although Duke owner Don Robey (using the pseudonym "Deadric Malone") appears on the songwriting credits.

The lyrics tell of a man, who, while pitying others for falling for a certain woman, knows that he is also shamed. After its release as a single, it became one of Bland's biggest hits and most identifiable songs. Subsequently, several artists have recorded renditions.

Bland described "I Pity the Fool" as one of the first songs to fit his emerging style. Although he did not recall the writer, he acknowledged Joe Medwick's contribution. Bland biographer Charles Farley goes further by identifying Medwick as the actual writer. Medwick (born Medwick Veasey) was a Houston, Texas-area, independent songwriter/broker. He regularly sold his completed songs to Duke owner Robey for small sums, along with any claim for the songwriting credit.

Bland recorded "I Pity the Fool" during the second session for his album Two Steps from the Blues. Overseeing the November 12, 1960, session in Chicago was band leader and arranger Joe Scott. He used a six-piece horn section with twin trumpets.Wayne Bennett's contrasting lead guitar along with the horn arrangement are key elements of the song. Music writer Chris O'Leary describes Bland's vocal:

Bland opened with dismissive coolness, taking his time on the descending title phrase ... but this is just bluster: when the song moved to its bridge, Bland howled. He was still entwined with her and the shame of it is killing him.

Blues historian David Evans calls Bland, "the picture of utter humiliation in this frightening outburst, sounding like he is going to do harm to himself or someone else. This is powerful soul blues at its emotional best."

"I Pity the Fool" was the first single released from Two Steps from the Blues. It entered the Billboard's Hot R&B Sides chart in February 1961, where it reached number one. The single also appeared at number 43 in the Billboard Hot 100 singles chart. As one of his most successful songs, it appears on numerous compilation albums, such as Bobby Bland: I Pity the Fool – The Duke Recordings, Vol. One (1992).

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