Your favorite or not so favorite hireling/npc

[Whit]

Throughout some adventures we had a npc hireling who was needed for healing. No one liked playing clerics back in the day.
After a while he would pop up in adventures here and there as a hireling, npc forced on us to work with or an opportunist who popped up when we needed help, and was annoying helpful.

He became an Infamous npc of legend in our games of 20+ years.

A Cleric who demanded a magic item or favor at the most dire times for healing. A few times he got what he deserved but mostly got away.

What a wonderful bastard he was.

[kobo1d]

Throughout some adventures we had a npc hireling who was needed for healing. No one liked playing clerics back in the day.
After a while he would pop up in adventures here and there as a hireling, npc forced on us to work with or an opportunist who popped up when we needed help, and was annoying helpful.

He became an Infamous npc of legend in our games of 20+ years.

A Cleric who demanded a magic item or favor at the most dire times for healing. A few times he got what he deserved but mostly got away.

What a wonderful bastard he was.

Meepo and to some extent Erky Timbers (of Sunless Citadel) have countless hijinks and stories from generations of D&D gamers now.

[Miz_Liz]

One of my longest running games has a great npc halfling ranger that keeps popping up. We started the campaign with a contract to rescue her from kidnappers, then she helped us clear out some nasty political influences in a city, then we kinda accidentally set her up as the shadow ruler of said city. Now whenever we visit we make sure to stop in and say high. She's a lot of fun.

[Darthnazrael]

In many games played in many systems with my wife, Gregory has shown up. He is always the eager and plucky sidekick who is in way over his head. He began as the WH40K equivalent of a beat cop tagging along with her high-ranking Arbiter. He has even, at one point, taken the form of a massive siege wyrm summoned by her Selesnya Druid in a Ravnica game.

And then theres the 'Olgers. First, there was Holger, a disagreeable middle manager from Princes of the Apocalypse whom I portrayed as every self-important mediocre dude you've ever worked for. From then on, whenever the party met a mediocre dude NPC, he became one of Holger's brothers. There's been Tolger, Bolger, Folger (makes crappy bean water), and Dolger so far.

[Pex]

In Lost Mine Of Phandelver we captured the two goblins who were not so great at keeping watch at the goblin cave. They told us Little Boss wanted Big Boss gone. We agreed to get rid of Big Boss, so they escorted us right to Little Boss, the head goblin. We made a deal with Little Boss we would get rid of Big Boss in exchange of them releasing Sildar unharmed. They agreed. Our escorts then proceeded to lead us straight to Big Boss. Any goblins we encountered we told them and our escorts confirmed we're going after Big Boss and leaving them alone. We were able to travel the entire cave complex without having to fight anyone. We killed Big Boss - the bugbear and his wolf companion in three rounds. The goblins were very happy and left to do their own thing and leave Phandelver alone. Our two escorts remained behind and joined our party as NPCs.

One goblin remained more as a helper, fancying himself as a chef and actually being pretty good at it. He was active as an NPC during downtime. The other one accompanied us on our adventures, including clearing out Cragmoor Castle and eventually the mine itself. He was very helpful in translating conversations we overheard since they were speaking in the goblin tongue. He also did distractions. He would enter a room first pretending to be the bad guys' servant like all goblins. Sometimes he would evens say intruders are here. That allowed us to get into the room and fight. We didn't always get surprise, but it was more important that we were able to be in the room first without them attacking us.

With everything that happens in the module, this normal by the book 7 hit point goblin survived it all and remained a true friend and ally to us. When we finished the module he was promoted to a semi-PC, meaning he could gain levels and be controlled by a player. He was a Fighter, becoming a Battlemaster. It was proud moment when he reached having 70 hit points, exactly 10 times more than when he first started. Circumstances and shenanigans later he became the Lord of Phandelver and surrounding lands, Dessarin. He converted to my cleric's religion (Ra) and became Lawful Good. He even joined The Lords' Alliance, the first and only goblin to do so. All hail Lord Sorg! The other goblin helped another PC open a restaurant in town, essentially running the place while we adventure.