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Does anyone know if Microsoft still holds its investment in Apple (originally $150 million)?
General consensus is that the stock was converted (to common shares) and sold sometime in 2003.
(comment deleted)
At it's peak, AOL/Time Warner's market cap was higher than both.

Market cap is not always a trustworthy number.

When AOL/Time Warner merged, Microsoft was peaking at over $500 billion. They've since continually edged back, but far slower than the collapse of the AOL monstrosity.

You'd have to go back pre-90s to even consider the possibility that a cable co beat out Microsoft. Maybe in the early years.