Note: After browsing the images of St. James the Less, one thing is clear: we have no freaking idea what he looked like. Balding or hirsute, pensive or vigorous, young or old, gentle or harsh, fair or dark -- the only thing the iconographers agreed on is that he was a white guy. And I suppose that even that is questionable.
St. Philip and James the Less share this feast because the Roman basilica that is now dedicated to the Twelve Apostles was once dedicated to Just These Two Apostles. In the Gospels, Philip had faith that Jesus was the Messiah, but continued to doubt the little things, like feeding the multitude. "Six months wages would not buy enough bread for each of them to get a little." Other examples of his doubt followed, which should be a comfort to the skeptics among us who aspire to faith.
James the Less is the son of Alphaeus, not to be confused with James the Greater, son of Zebedee. James the Less was the apostle who provided the compromise solution to the question of how Jewish a Gentile would need to become in order to be Christian. Some of the hardcore apostles (I think James the Greater was one) wanted the full conversion. Circumcision was of course the part that made many squeamish. Some thought declaration of belief in Christ as the son of the One True and Living God would be enough. Paul called a council, at which James the Less suggested that they abstain from things (food, wine) offered to idols, and from whatever has been strangled, and from blood. Paul led the council in approving the compromise and Christianity began its slow ascent to prominence.
There are a couple of deacons celebrated on this day -- Rhodopianus and Diodorus, both martyred during the reign of Diocletian. Deacon John: If you are reading this, I haven't forgotten the need for research. It's on my mind.