Breaking stereotypes came naturally to Jamaican-American singer Harry Belafonte whose death on April 25 marked the end of an era. Apart from captivating generations with his bass-baritone, the enduringly handsome Belafonte headlined the Oscar-nominated film Carmen Jones and placed himself at the forefront of the US civil rights movement in the mid-1950s. We pick five Belafonte songs that have stayed with us through the years.Jamaica Farewell (1956)

Released in Belafonte’s 1956 album Calypso, this bittersweet ballad remains the standard for parting songs. Belafonte’s parents immigrated to the US from Jamaica and the song captures the agony of leaving one’s homeland. Irving Burgie’s lyrics celebrate the beauties of the Caribbean islands through tears as the singer laments leaving his love in Kington town. Jamaican Farewell reached number 14 on the Billboard Pop chart.

Banana Boat Song (1956)

This folk song emerges right from the Jamaican docks where labourers chant during long night shifts loading bananas on to export ships. The song made Belafonte’s Calypso album the music industry's first album that sold more than a million copies. Belafonte learnt the song from Carribean folk music scholar Lord Burgess.

Matilda (1953)

After recording the traditional Calypso song in 1953 as a single, the singer re-recorded it for his second RCA Victor LP called Belafonte (1955). In this song, the singer is lamenting a woman who took a man for all he was worth and fled to Venezuela by repeating the syllables of her name. Matilda went on Belafonte’s most popular songs in live concerts.

Midnight Special (1962)

The title track of Belafonte’s 1962 album The Midnight Special is a folk staple from the American south. The singer’s take on this traditional blues features the singer at his cockiest as he showcases a wide range of emotions and styles. The recording also marks the first official recording by Bob Dylan, who plays the harmonica intro and interlude, evoking the sound of a passenger train.

Brown Skin Girl (1962)

Yet another track from Calypso, Brown Skin Girl presents how American soldiers exploited the women of the West Indies after invading the islands. Belefonte’s dynamic vocals take this haunting song, accompanied by soft guitar sounds, to a whole new level.