Glaurung the Father of Dragons, and Azaghâl, King of Belegost

The only thing bigger than Ancalagon the black : r/Silmarillionmemes

Ancalagon >>>> Glaurung >>>> Smaug : r/lotrmemes

NO SPOILERS] Westeros's Drogon(short necked, younger and faithful) vs Middle Earth's Smaug(Long necked, badass, intelligent, without a master). Who would win? Personally, I prefer short necked dragons but Smaug might can easily

Glaurung and Nienor, fan-art by Me. (Digital-painting) : r/conceptart

Glaurung the Deceiver : r/lotr

Glaurung. The Battles of Beleriand. by Ctónico (José Luis Moreno) : r/lotr

My depiction of Ancalagon departing for the War of Wrath : r/lotr

Ancalagon was killed 2 sentences after he was introduced but that two sentences was probably more than few years : r/Silmarillionmemes

The Silmarillion - Turin vs Glaurung by Guillem H. Pongiluppi : r/ImaginaryDragons

Spike and Glaurung Petventure : r/DungeonsAndDragons