September 24, 2009: Apple lawyers head to court to defend itself against rapper Eminem’s music publisher, Eight Mile Style.

The lawsuit alleges that Apple unlawfully sold 93 of Eminem’s songs on the iTunes Music Store. This is the second time Apple finds itself on the opposite side of a courtroom from Eminem. A previous lawsuit involved improper use of Eminem’s hit single “Lose Yourself” in an iTunes ad.

Apple’s back, back in court

The iTunes Music Store case dated back to July 2007, when Eight Mile Style first sued Apple. The publisher alleged that digital rights to Eminem’s catalog had been sold without proper approval.

Apple had signed a contract with Aftermath Entertainment, a label founded by Dr. Dre (who later joined Apple with the 2014 Beats acquisition). Apple thought the deal included Eminem’s digital sales rights. However, Eight Mile Style lawyers said an unusual clause in Eminem’s contract meant a separate deal must be negotiated for digital sales. Such a deal never got hammered out.

Eight Mile Style requested $2.58 million, which it claimed Apple made from sales of Eminem’s music. The publisher also asked for $150,000 per infringement in damages, adding up to $14 million.

Apple’s lawyers, meanwhile, revealed that the company paid Aftermath 70 cents per download and Eight Mile Style 9.1 cents (and that both had continued to cash their checks).

Apple settles with Eminem

In the end, Apple and Eminem settled out of court, just as with the previous lawsuit over the “Lose Yourself” ad. The news was significant, however, because — just like Apple’s legal battling with The Beatles — it highlighted one of the new challenges Apple faced as a major player in the music industry.

Today, it seems Apple and Eminem are back on good terms. Not only does Em’s mentor, Dr. Dre, work for the company, but Eminem also appeared on Beats 1 radio to promote his work.

What is the most unlikely celebrity lawsuit you remember Apple being involved with? (For me, it still has to be Carl Sagan!) Leave your comments below.