Risa

From Cabin Boy (1994) featuring Ann Magnuson aka Admiral Clancy.

TOS and SNW Chapel count as separate characters.

It's like it's part of their job description.

For Flying Squid. Plus bonus TNG: Nighthawks

Stouffer's comes in second.

A continuation of FauxPseudo's idea.

See that face on the screen in the upper picture? Apparently after the time travel events from Voyage Home were done she stole that Klingon rust bucket time machine from the bottom of San Francisco Bay and went back in time. Scanning the Historical Documents I have uncovered that she didn't just time travel more than once but time traveled in two different devices!

She apparently traveled first to proto renascence France and got crazy with all her Starfleet combat training and in the middle of a time travel adventure has a second time travel adventure going to the late 1980s to help some California kids with their history report.

Inspired by her time with Wyld Stallyns she stays in California but goes back in time to the late 1970s California and was part of the one of the biggest all female bands of all time.

Then she, Go-Go's to the 1940s, has an affair with a professor and dies, unexpectedly, while putting her singing voice to use delivering singing telegrams.

How come no one talks about this amazing temporal adventure? I am going to get a visit from the Temporal Integrity Commission for talking about this?