"I want is simply to have the task run for each item in  "mylist" for each host 
in "somegroup"."

Ansible loops through your groups and hosts and executes tasks against them. 
Therefore there is no need to manage an outer loop, Ansible does it for you and 
is central to how Ansible works.

"Thus, have the task run for 5 times: for item1, item2, item3, item4 and item5."

This inner loop is as simple as with_items as already suggested.

Does that help or did I confuse you more?

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