"Can I Play with Madness" is a song by the English heavy metal band Iron Maiden. The song is the sixteenth single released by the band. Released in 1988, it was the first single from their seventh studio album, Seventh Son of a Seventh Son (1988), and hit number 3 in the UK charts. The song is about a young man who wants to learn the future from an old prophet with a crystal ball. The young man thinks he is going mad and seeks the old prophet to help him cope with his visions/nightmares. The prophet's advice is ignored by the young man and they become angry with each other. The song was originally a ballad named "On the Wings of Eagles", written by Adrian Smith.

The song's guitar solo is played by Adrian Smith.

The video of the song was set at Tintern Abbey and Chislehurst Caves, and features Graham Chapman; this would be one of his last appearances on television before his death in October 1989 of cancer. In the video, Chapman plays an irritable art instructor who criticises a young student for including Iron Maiden's mascot Eddie in his sketch of the abbey ruins. The teacher then falls down a hole in the ground, discovers an underground vault and finally encounters an animated version of Eddie, who leers at him from inside a refrigerator. The band appears on a TV screen showing footage from "The Number of the Beast" video and the Live After Death concert film. Adrian Smith is shown playing left-handed, suggesting a reversed image.

"Black Bart Blues" is about the suit of armour that rode in the back lounge of Iron Maiden's tour buses (named Black Bart). Bruce Dickinson tells that he, his bandmates and their tour manager were driving in a Ford Thunderbird through Florida in 1983, when they passed a gas station with three suits of armour standing outside. So Bruce stopped the car and went to buy one of the three suits of armour that were on sale. The song's lyrics detail a rather infamous story in which a girl stumbled onto the band's tour bus and struck a deal with one of the band members that she'd give them oral sex in exchange for alcohol.

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