How to add multiple font files for the same font?

To have font variation working correctly, I had to reverse the order of @font-face in CSS.

@font-face {
    font-family: "DejaVuMono";
    src: url("styles/DejaVuSansMono-BoldOblique.ttf");
    font-weight: bold;
    font-style: italic, oblique;
}   
@font-face {
    font-family: "DejaVuMono";
    src: url("styles/DejaVuSansMono-Oblique.ttf");
    font-style: italic, oblique;
}
@font-face {
    font-family: "DejaVuMono";
    src: url("styles/DejaVuSansMono-Bold.ttf");
    font-weight: bold;
}
 @font-face {
    font-family: "DejaVuMono";
    src: url("styles/DejaVuSansMono.ttf");
}

As of CSS3, the spec has changed, allowing for only a single font-style. A comma-separated list (per CSS2) will be treated as if it were normal and override any earlier (default) entry. This will make fonts defined in this way appear italic permanently.

@font-face {
    font-family: "DejaVu Sans";
    src: url("fonts/DejaVuSans.ttf");
}
@font-face {
    font-family: "DejaVu Sans";
    src: url("fonts/DejaVuSans-Bold.ttf");
    font-weight: bold;
}
@font-face {
    font-family: "DejaVu Sans";
    src: url("fonts/DejaVuSans-Oblique.ttf");
    font-style: italic;
}
@font-face {
    font-family: "DejaVu Sans";
    src: url("fonts/DejaVuSans-BoldOblique.ttf");
    font-weight: bold;
    font-style: italic;
}
@font-face {
    font-family: "DejaVu Sans";
    src: url("fonts/DejaVuSans-Oblique.ttf");
    font-style: oblique;
}
@font-face {
    font-family: "DejaVu Sans";
    src: url("fonts/DejaVuSans-BoldOblique.ttf");
    font-weight: bold;
    font-style: oblique;
}

In most cases, italic will probably be sufficient and oblique rules won't be necessary if you take care to define whichever you will use and stick to it.

The solution seems to be to add multiple @font-face rules, for example:

@font-face {
    font-family: "DejaVu Sans";
    src: url("fonts/DejaVuSans.ttf");
}
@font-face {
    font-family: "DejaVu Sans";
    src: url("fonts/DejaVuSans-Bold.ttf");
    font-weight: bold;
}
@font-face {
    font-family: "DejaVu Sans";
    src: url("fonts/DejaVuSans-Oblique.ttf");
    font-style: italic, oblique;
}
@font-face {
    font-family: "DejaVu Sans";
    src: url("fonts/DejaVuSans-BoldOblique.ttf");
    font-weight: bold;
    font-style: italic, oblique;
}

By the way, it would seem Google Chrome doesn't know about the format("ttf") argument, so you might want to skip that.

(This answer was correct for the CSS 2 specification. CSS3 only allows for one font-style rather than a comma-separated list.)