What are your top 5 favorite Nightwing stories/comics
1) Tales of the Titans #44
2)  Nightwing #8 - Scarecrow nightmare issue
3) Batman Year 3
4) A Lonely Place of Dying
5) Nightwing: Enter Shrike (#55-57)

1. Judas Contract
2. The great leap
   
3. Freefall
4. The lost year
5. A lonely place of dying
   

Prodigal would have to be one of them, as would Judas Contract. 

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For me personally, it's as follows:

1. The Boys (Nightwing #25)

2. On Wings (Birds of Prey #8)

3. The Judas Contract

4. Year One (Nightwing #101 - 106)

5. Detective Comics #725

Year One

Judas Contract

Long Shadows

Lost Year

Prodigal

Honorable mention to A Lonely Place of Dying

@Nathaniel_Christopher and @darkwingdan and @Chaos Agent

Why do you guys love Year One so much? I am genuinely curious because it really doesn't do it for me. Most of my Tumblr friends don't really like it either, so I'm genuinely curious to hear a different perspective.

Actually, same thing for The Lost Year. What do you like about it?

I would really appreciate hearing your perspective! Thanks.

@dicksihavestudied: I enjoy Year One because of focus on character moments. There's the falling out with Batman, which is a moment I love reading about no matter how many different ways it's been written. There's the interaction with Superman - which shows the strength of their relationship. When Dick returns to Gotham as Nightwing, his interactions with Batgirl and Jim Gordon are a joy to read. The team-up with Jason Todd at the end displays the beginning of what would be a difficult big brother / little brother relationship between the two.

With any Year One story, the goal is to show the readers who the character was before they became the person we know them as, and then show us how they got to where they are now. All of the other Year One stories have had the benefit of the character being a civilian before masking up. Nightwing: Year One does not have that benefit, but for that reason it breaks the mold in telling a coming of age story of a man trying to forge his own identity after being so closely associated with someone of substantial stature. Chuck Dixon writing definitely helps this, as he is one of the few writers out there with a strong grasp on what makes Dick Grayson tick and, therefore, gives him a defining voice - as was the case through his entire Nightwing run.

Why do I enjoy Year One so much? Well, because of all the strong character moments that are written by the guy that many consider to be the defining voice of the character, drawn by the guy that many consider the defining artist for the character (Scott McDaniel).

@Will44: That Nightwing 8 is the single issue that I can thank (blame) for getting me back into comics. The story was great, the McDaniel art was stunning...and I had no idea what was going on. It was proof that you don't need to know everything about a character, their history, or even the current story to jump in and enjoy yourself.

@darkwingdan said:

@dicksihavestudied: I enjoy Year One because of focus on character moments. There's the falling out with Batman, which is a moment I love reading about no matter how many different ways it's been written. There's the interaction with Superman - which shows the strength of their relationship. When Dick returns to Gotham as Nightwing, his interactions with Batgirl and Jim Gordon are a joy to read. The team-up with Jason Todd at the end displays the beginning of what would be a difficult big brother / little brother relationship between the two.

With any Year One story, the goal is to show the readers who the character was before they became the person we know them as, and then show us how they got to where they are now. All of the other Year One stories have had the benefit of the character being a civilian before masking up. Nightwing: Year One does not have that benefit, but for that reason it breaks the mold in telling a coming of age story of a man trying to forge his own identity after being so closely associated with someone of substantial stature. Chuck Dixon writing definitely helps this, as he is one of the few writers out there with a strong grasp on what makes Dick Grayson tick and, therefore, gives him a defining voice - as was the case through his entire Nightwing run.

Why do I enjoy Year One so much? Well, because of all the strong character moments that are written by the guy that many consider to be the defining voice of the character, drawn by the guy that many consider the defining artist for the character (Scott McDaniel).

This sums it up nicely I think. Year One is just a good solid read, with many great moments. You see Dick's relationships with various people (Superman, Batman, Jason Todd, Barbara Gordon, Donna Troy, and Alfred), with none being portrayed as unimportant for once. This is a comic where Dick is at his finest, completely in character, working hard and trying his best, but hurt by his falling out with his mentor. Yet, its very clear he's no longer that young boy who watched his parents fall before his eyes. He's a man now and ready to step out of his mentor's shadow and stand on his own two feet.

This story did the same thing for Nightwing that was done for Batman with his Year One. In a way it does a little more, because Dick's already an established hero by this point, and he's now creating a new identity. It touches on his origin, various aspects of his life that have led him to this point, and then goes through the steps of him creating this new identity for himself. You really don't even have to have ready anything prior to it, and that's a necessity for any good origin story in my opinion.

@darkwingdan and @Nathaniel_Christopher

Thanks for the thoughtful replies. I will take them into consideration.

However, I find Year One to have been too focused on the Bat-family, and I don't think the Titans were given their due. Many of the character moments were nice, especially the Superman and Jim Gordon ones, but I did not like the interactions between Nightwing and Batgirl. It felt like another "star-crossed lovers ret-con" to me. Had there been no romantic overtones, I would have been fine with it. As you pointed out in an earlier thread, Nathaniel, ret-cons such as Nightwing Annual #2 have made people think Dick and Babs were together for much longer than they really were. Year One contributes to that. I'm not a Dick/Kory shipper, but I felt Dixon was suggesting Dick didn't actually love Kory, etc. To me, that's not an accurate grasp on the character because it ignores the NTT history. Plus, it kind of makes Dick look like a dick and I'm never a fan of that. I might be nit-picking a bit and letting the little things ruin my overall enjoyment of the work, but for some of us, this kind of stuff is a big deal. Dick was established, for such a long time, as someone who was loving, respectful, and not a cad. It's one of the many reasons he has so many female fans. Ret-cons that tarnish that image really annoy some of us.

I think I'm too wedded to "The Judas Contract" to ever truly enjoy Bruce firing Dick. This version was so harsh. Yes, it's high drama, but I hate to see Bruce being that much of a jerk.

But, seriously, thanks for the replies. I don't hate Year One, but I guess I would never put it in my top 5.

@Chaos Agent said:

1. Judas Contract
2. The great leap
3. Freefall
4. The lost year
5. A lonely place of dying

Judas contract have any relation to the Judas coin story? Because that's at my local shop in trade.Though i think it's a batman story.

These 3 are my personal favorites:

Nightwing: Year One

Teen Titans: Judas Contract

Nightwing #25: "The Boys"