Alright, well we got 3 of 6 for Sinatra. Left as likely options are:
Model
Conductor
Cast
.
.
.
Life
Trip
For Pitt, the most obvious is Olive. After that, Conductor seems the logical second - which presents an overlap word with Sinatra. Cast (Brad Pitt) could be a third, and might also present an overlap word. That would leave us one word short on both Sinatra and Pitt, for a total of 8 words.
Remaining options for 1 Pitt & 1 Sinatra:
Button
Turkey
Model
Life
Trip
Nurse
Milk
Line
Garage
Microscope
Litter
Bottle
With Brad Pitt the connection for Cast, he could also fill Model - which may be another double with Sinatra. That would leave us at 7 words and a pass, unless you feel strongly about anything else on that list. Red has 5 with open clues still, so they are technically in striking distance - but 7 & Pass gives Eevee the solo if it gets back around.
Thoughts?