Alcohol and sleeping pills? I've had horrible insomnia my entire life and take sleeping pills nightly because of it. It says on the bottle not to mix with alcohol. I also just turned 21. Could I drink in the early afternoon or evening, then take the pills

Not a good combo. The best treatment for insomnia is not sleeping pills. Eventually even someone who rarely has insomnia will become dependent on sleeping pills, and not be able to sleep without them. Talk to a doctor with experience in sleep medicine about tapering you off those medications, and using cognitive behavioral therapy for sleep. Alcohol will only worsen the problem and i would avoid it. Avoid caffeine.
As . As a general rule, you should not have more than two alcoholic beverages in a day and they should be consumed 4 hours before bedtime. If you have horrible insomnia and are taking sleeping pills nightly, it is best to avoid alcohol. Sounds like you would benefit from the help of a sleep specialist.