Idea came up in conversation. It's a python script that starts a random program off your hard drive.

random_program.py

import os.path
import sys
import random
import re
import argparse
from pathlib import Path

def main(fast=False, once=False):
    if fast:
        get_exe = random_walk
    else:
        exes = gather_walk()
        get_exe = lambda: random.choice(exes)  
    while True:
        file = get_exe()
        print(file)
        confirm = input("Good Idea?(y/N/q):")
        if len(confirm) > 0 and confirm[0].upper() == 'Y':
            pipe = os.popen(str(file))
            pipe.close() #This blocks until the program closes.
        elif len(confirm) > 0 and confirm[0].upper() == 'Q':
            break
        elif once:
            break

drives = None
def get_roots():
    if os.name == 'nt':
        global drives
        if drives == None:
            drives = os.popen("fsutil fsinfo drives").readlines()
            drives = ''.join(drives)
            drives = list(re.findall('\s(\w:)', drives))
        return map(lambda x: x+'\\', drives)
    else:
        return ['/']

def is_exec(file):
    if os.name == 'nt':
        if isinstance(file, Path):
            return file.suffix == '.exe'
        elif type(file) == str:
            return re.search('\.exe$', file)
    else:
        return os.access(file, os.X_OK)

"""
Walks down the filesystem to find an executable at random.
it's biased toward files with paths with less steps in them.
or in smaller folders.
"""
def random_walk(file=None, tries=0):
    if file == None:
        file = get_root()
    try:
        if file.is_dir():
            di = [x for x in file.iterdir()]
            if len(di) > 0:
                fl = random.choice(di)
                return random_walk(fl, tries)
        elif is_exec(file):
            return file
        else:
            pass
    except PermissionError:
        pass
    #fallthrough, if we haven't retuned something went wrong.
    #print("%d: %s" % (tries, file))
    return random_walk(None, tries+1)

def gather_walk():
    execs = []
    for root in get_roots():
        for dirpath, dirnames, filenames in os.walk(root):
            #print(dirpath)
            for file in filenames:
                #print(dirpath+file)
                if is_exec(file):
                    execs.append(dirpath+file)
                    if len(execs) % 1000 == 0:
                        print(len(execs))
    return execs


if __name__ == '__main__':
    parser = argparse.ArgumentParser(description='')
    parser.add_argument('-o', '--once', action='store_true', help='Only run once instead of as a loop.')
    parser.add_argument('-f', '--fast', action='store_true', help='Use a fast to chose, but biased selection method.')
    args = parser.parse_args()
    main(**vars(args))