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"Can I Play with Madness" was the sixteenth single released by Iron Maiden. Released in 1988, it is the first single from the Seventh Son of a Seventh Son album 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 video of the song was set at Tintern Abbey 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 criticizes a young student for drawing Iron Maiden mascot Eddie rather than sketching the abbey ruins. The teacher discovers an underground lab and finally encounters an animated version of Eddie, who leers and reaches out to him from inside a refrigerator. The band appears on a TV screen showing live footage of a concert. Adrian Smith is shown playing left-handed, suggesting a reversed image.

As the third track in the Seventh Son of A Seventh Son album, it has been suggested that this song is about the Seventh Son of a Seventh Son father. Maybe the visions and nightmares he has are the ones explained in the Infinite Dreams song. The symbol accompanying this song in the album booklet (and, therefore, it's suggested it completes its significance) is the Crescent Moon.

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