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Give your guests allocated people to dress up as - think along the lines of Audrey Hepburn, Marilyn Monroe, Twiggy, Ray Charles. Any person coming from around the 1940's is good. It's easier and funner this way. If you want, make the actors first inicial the same as your guests first inicial.
On the invitation, put a picture of the person that they are allocated, with their name underneath. Make sure to include the usual information such as When, Where, What, Etc. Encourage everyone to dress up - this will make it funner.
Make a flashy entrance, with (preferably) a long red carpet that your guests can walk along. If you want to go all out, cut out the letters of 'hollywood' on large pieces of carbboard, preferably in the style of the actual hollywood sign, ( If you're unsure of what the hollywood sign looks like, googling it would be the smartest idea. ) Normal cardboard may be a bit flimsy, so it might be better to use the cardboard from large cardboard boxes, and then paint the letters white with thick paint.
If you really want to make your guests feel as if they are in hollywood (although, they might feel a bit awkward, depending on your social scene) get your family/hire some people to stand around the red carpet with big cameras, and as the guests walk along the carpet, get them to take plenty of pictures of them and act like they are a proper star, trying to ask them questions and what not.
If you aren't willing to go quite that insane, and don't want to spend the money on a red carpet (they can be very expensive, you can go for a more 'classy' look, with a long white sheet (you can easily just thrift one) and lay it out with fake flowers or something of that sort lying along it. Fairy lights would complete this look, but if you don't want to go that far, then you can go without.
Decorate around your house with plenty of fancy candles/candle holders. Candle holders are easily thrifted. Also, if you have posters of old actors, stick them up around the place. If you want, get custom made glass coasters with pictures of old actors on them.
If you want to go for a more genuine, current hollywood look, then decorate your place with big yellow stars, trophys, cups of popcorn, etc.
For your Old Hollywood Pary, play music like Billie Holiday, Elvis Presley, Marilyn Monroe, Frank Sinatra, Dean Martin, Fred Astaire, Clark Gable, you could possibly fit in Shirley Temple somewhere : ) Just a few suggestions, although there are many more that you could find. As long as they sound classic, and stereotypically 'old', they will suit.
Set up the table in a fancy-way, so as to make your guests feel as if they're really in olden times. Use, ofcourse, wine glasses. Flowers around the tables. Classy dishes to put the food in, etc.
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