Before the invention of printing, the ‘look’ of a script was determined by those in charge of producing large amounts of text—the professional scribes.
When Judeans first adopted the Assyrian version of the Canaanite script as their new script, some time in the 6th centuring BCE, the characters looked like this (pardon the letter order, which is left-to-right order, instead of right-to-left):
You could—the letters are substantially the same (functionally speaking) as the modern Hebrew alphabet—but it is graphically less sophisticated than its derivatives, namely the Greek & Roman alphabets, and the Assyrian script which gave rise to the revised form of Hebrew from the Second Temple period onwards, known today as “Square Script”:
The Square Hebrew / SimHebrew™ Converter will convert any Square Hebrew text into Roman characters (and back again), with full fidelity with regard to spelling and distinction between seemingly homophonous characters:
As with French, German, Italian, or any other Roman-based language, however, you would have to bear in mind that certain characters have different phonetic values compared with English:
In Steve Carell and Tina Fey’s amusing comedy Date Night, there are two scenes where they visit Mark Wahlberg (who plays some kind of secret agent who helps them out), and he exchanges a few words in Hebrew with his girlfriend in the background, who is an Israeli Mossad agent. The actress playing the Mossad agent is indeed Israeli, but Wahlberg himself does a very credible job pronouncing the few words that he says, and with almost no accent. (Although I agree with Carell’s character: For the love of God, please put on a shirt!…)
But he’s the exception to the rule. 99% of the time, whenever Hebrew is presented in American films or TV series, something is wrong.
From the time of the Canaanite enslavement in Egypt in the 1900s BCE the end of the First Temple—a period of 1400 years—Hebrew was written in the Canaanite script that was common to all Canaanite peoples. During their three generations of exile in Babylon, the Judean upper classes were exposed to the Assyrian/Aramaic script, which was inspired by the Canaanite script but had evolved, under centuries of Mesopotamian scribes, into a more disciplined set of forms designed around a squarish template (rather like that of the original calculator displays).