Whether or not cascading ciphers weakens or strengthens data is still up for debate.
That said, to address the OP, if you take three separate programs that all use AES, and you use the same password for all three, they will be equal. The implementation of AES is pretty standard at this point. This excludes the possibility of hidden back doors, etc. Just speaking on the encryption itself.
Personally I prefer TC because its open source. Paranoid? Maybe. But whatever you choose, AES with a passphrase 20+ characters long = no one's gonna break it any time soon. Certainly not in your lifetime.
Theoretically, a
one time pad is the most secure form of encryption, but it is not practical.
Every bit of practicality you add reduces the security. Examples of certain implementations (such as WEP) use tricks (such as very short initialization vectors) to make the stream less secure, but more practical to use and implement cheaply in hardware.
AES most certainly isn't the most secure algorithm, theoretically, but it is the one that has been subjected to (arguably) the most mathematical analysis. It's worth pointing out that a number of schemes that were considered theoretically secure in the past, were found to have very subtle mathematical flaws in them.
In fact, the strength of AES was discovered to be an order of magnitude lower than was originally thought, just a few years ago. But that doesn't really matter, since it is still beyond the combined processing capability of the entire world's computers combined to crack AES-256 via brute-force keyspace attacks within your lifetime. That's not to say there won't be a mathematical weakness found in AES (or any other algorithm) at some point that utterly destroys it, though most cryptographers find that highly unlikely given the strenuous study that goes into the math behind these algorithms.
But to be fair, there is always something
more secure. But if you're talking about some tool that is going to encrypt your tax returns or your foot fetish porn, the weakness is not in the algorithm anyway. The weakness is in the implementation, in the password input method, in the password itself... there are theoretical weaknesses in the device drivers that mount the file system, there are theoretical risks in the hooks that place those drivers into kernel space so it can appear as removable media. There are risks in the operating system surrounding things like caching (Windows 7 WILL cache those foot fetish pictures in pretty high res format) and in your browsing and file history. Programs like Microsoft Word will leave temproary files with your tax return data all over the place.
The problem in security as LITTLE to do with the encryption algorithm, which is one of the many reasons I came across as so dismissive in the first place.
More specific questions draw more specific answers.
Personally, I also agree about TrueCrypt. Tested algorithms, open source code, solid drivers. It's about as good as you can find (balancing usability with security).