You can use proxychains. It's pretty adjustable, it shows you the status of each part of the chain and always obeys your order specification, unless it fails totally.
This works on Ubuntu, so the process will be similar on Debian
$ sudo apt-get install proxychains
$ sudo nano /etc/proxychains.conf
Make sure dynamic_chain is commented
And that strict_chain is uncommented
Scroll all the way down and change
socks4 127.0.0.1 9050
socks5 127.0.0.1 9050
Now, just add any proxy you want (on new line, you can add as many as you want)
You can see the supported proxy types:
proxy types: http, socks4, socks5
Now just type
$ proxychains iceweasel
And it will obey your proxy chain. You can see each part working in the terminal.
Protip: This is is useful against CloudFlare's Tor captcha.