The title "Song of Deborah" is more properly applied to chapter 5 of Judges. This chapter consists of a poem (obviously laid out in verse to be performed as a song) describing basically the same events that are related in the narrative version of Judges 4, but with different details and different perspectives. Deborah is Hebrew for "bee".
Panel 1: There is more information about Deborah in the Bible than I was able to fit in here. For example, she was married to a fellow named Lappidoth (see below), and held court beneath her palm in between the ancient cities of Ramah and Bethel in the tribal territory of Ephraim. Though they can be found in that region, palm trees are rare there, so the Palm of Deborah, as it is formally named, must have been quite a landmark.
There's an interesting controversy over the name of Deborah's husband. "Lappidoth" is not a word normally used as a name, but is generally used as a female descriptive term, with the literal meaning of 'torch' or 'flame'. Some interpreters take this to mean that Deborah wasn't married at all, but that this actually identifies her as a "woman of lights" or a "woman of flame" referring to her character or zeal. Other interpreters identify Lappidoth as another name for Barak, implying that perhaps he was actually her husband.
Panel 2: The king of Canaan's name was Jabin, and he ruled from the fortress city of Hazor. Sisera himself had his headquarters in a town called Harosheth Haggoyim. The Bible mentions more than once that they had an impressive army, including 900 iron chariots, the devastating super weapon of the day. In the Song itself, it's mentioned that the Israelites didn't even have spears or shields, so the Canannites probably had an overall severe technical advantage.
I have Sisera talking so much about plunder because in the Song, Deborah and Barak sing that raking in the plunder is the excuse Sisera's mother tells herself as to why her son is delayed in returning to her from the Battle of Tabor (see below). Of course the real reason he doesn't return is because Jael kills him.
Panel 3: Barak, the son of Abinoam, lived in a city called Kedesh in the tribe of Naphtali. Barak means "lightening" in Hebrew.
Deborah claimed that her battle plan came directly from God, which is why she was so harsh with Barak when he hesitated. The details were that Barak was to take 10,000 men of the tribes of Naphtali and Zebulun up to Mount Tabor. This was going to lure Sisera and his troops to the Kishon River below where Barak was to attack.
Later in the song itself, out of the 12 (actually 13 at this point because the tribe of Joseph had split into Ephraim and Manasseh) tribes of Israel, the tribes of Naphtali, Ephraim, Benjamin, Zebulun, the eastern part of Manasseh (represented by the region of Makir) and Issachar are singled out and praised for fighting. The tribes of Reuben, Gad and the western part of Manasseh (as represented by the region of Gilead), Dan and Asher are rebuked for staying at home and hiding. Judah and Simeon are not mentioned, perhaps because Deborah and Barak were only concerned with the northern tribes. And of course, the Levites, being priests, had no territory and usually didn't fight.
Panel 4: The Song in Judges 5 says that the battle took place near the city of Taanach by the waters of Megiddo, and that the stars themselves fought against Sisera, and that the river Kishon swept him and his army away. Could this mean that God sent a storm and a flood to help Barak defeat the Canaanites?
It is not mentioned whether Deborah actually took part in the battle or wielded a sword or weapon. Whatever the true case with women warriors in that time and place, she was an important leader, and we do know that she was right at the forefront, because she gives a stirring speech to Barak to urge him on right before he attacks. However, she drops out of the action after that, and it's most likely she acted more as a rallying point and encouragement for the troops, since from this point on the text only mentions Barak actually fighting.
Barak did indeed pursue Sisera's army clear back to his headquarters in Harosheth Haggoyim, routing out and laying waste to the whole military machine. It was a complete and utter defeat for the Canaanites.
After the battle, an angel curses something called Meroz, because its people did not help in the fight. This was likely a village or town allied with Israel that failed to come through in the clutch.
Panel 5: The nomads mentioned here is actually a clan led by a fellow named Heber the Kenite. They were camped near Barak's home town of Kedesh, by a great tree in a place called Zaanannim. Jael herself was Heber's wife. Jael obviously recognizes Sisera and clearly lures him into the tent and puts him at ease with the clear intent of killing him.
Panels 6 and 7: It's hard to say which side Heber and his family are on, and to me it's very puzzling as to exactly why Jael killed Sisera.
On the one hand, the Kenites were descendants of Hobab, Moses's father-in-law, and were obviously camped on Israelite land. We are also told that Heber's clan had left the other Kenites to go camp in this particular spot. So they were related to the Israelites and living amongst them.
But on the other hand, chapter 4 of Judges clearly states that there were friendly relations and some kind of alliance between Jabin the king of Hazor (the Canaanite king and Sisera's boss) and the clan of Heber the Kenite. This may be why Sisera ran to this particular clan to get away after being defeated.
So even if they are distantly related to and perhaps friendly with Israel, why would Jael kill her husband's friend and ally? My take on it is that probably Heber and his clan were "friends" with the Canaanites because Sisera had a big army and bullied them into it. It certainly fits in with his character, as he has no problem bossing Jael around even when on the run. Perhaps Jael was sick and tired of Sisera pushing her husband and her clan around. In any case, it's not recorded what Heber's reaction was when he came home that night, but I bet it was something to see!
Panel 8: I didn't base the character designs in this on anything other than my imagination. I gave Deborah braids and a hair clip in an attempt to make her look regal, and also tried to make her resemble my sister without being too obvious. The rest of the characters are pretty generic, not based on anything or anyone specifically. Sisera's helmet is adapted from my memory of a Philistine helmet from roughly the time period in question.