I assume this is a Four Roses whiskey bottle. You are not going to get to an exact date but perhaps a range of time.
The ad below is from 1936. Note that it is a SIMILAR but not exact bottle, and that the one shown in the picture has a cork closure so could be a bit earlier.
This image is from ebay.com. Here is the ebay search that I used: https://www.ebay.com/sch/i.html?_from=R40&_trksid=p2380057.m570.l1313&_nkw=four+roses+whiskey+ad&_sacat=0
Advertisements can be a good way to identify and date 20th century liquor bottles.
Note that there are other threads in this forum dealing with Four Roses
