Ended up doing this. Any ideas on how to make this better?
$s = imagettfbbox(50,0,$font,$text);
if ($s[2] < 399) {
$fontfind .= '50|';
}
$s1 = imagettfbbox(45,0,$font,$text);
if ($s1[2] < 399) {
$fontfind .= '45|';
}
$s2 = imagettfbbox(40,0,$font,$text);
if ($s2[2] < 399) {
$fontfind .= '40|';
}
$s3 = imagettfbbox(35,0,$font,$text);
if ($s3[2] < 399) {
$fontfind .= '35|';
}
$s4 = imagettfbbox(30,0,$font,$text);
if ($s4[2] < 399) {
$fontfind .= '30|';
}
$s5 = imagettfbbox(25,0,$font,$text);
if ($s5[2] < 399) {
$fontfind .= '25|';
}
$s6 = imagettfbbox(20,0,$font,$text);
if ($s6[2] < 399) {
$fontfind .= '20|';
}
$s7 = imagettfbbox(15,0,$font,$text);
if ($s7[2] < 399) {
$fontfind .= '15|';
}
$s8 = imagettfbbox(10,0,$font,$text);
if ($s8[2] < 399) {
$fontfind .= '10|';
}
$s9 = imagettfbbox(5,0,$font,$text);
if ($s9[2] < 399) {
$fontfind .= '5|';
}
$fontfound = explode("|",$fontfind);
$fontsz = $fontfound[0];