Have been listening to The History of Rome by Mike Duncan lately, absolutely superb. It's great to hear it all in chronological order so you can understand how each thing led to the next.
I listened to that religiously years ago right to the end,i remember waiting in anticipation for the next episode every week.
The Punic wars on the Rome podcast with Hannibal and Carthage are amazing listening,also mentions a titbit of Hannibal and Scipio Africanus actually meeting i think in Greece (Hannibal was training an army) decades after the war ended at a party and both claiming they were the better military leader.
That is my all time favourite podcast.
The History of WW2 with Ray Harris Jr which is also fantastic listen which started in 2010 i think and still going strong today with an episode every 2 weeks.
One fan of History Of Rome actually continued where the History of Rome podcast stopped with the Byzantine Empire which is up to episode 171 right now, (The History Of Byzantium) it's called.