Boston Crabby: Ensure a flunky knows his role - Give the angry reaction to Sam's promo video.

Parts Unknown: Win an amateur match via forfeit - Call an ambulance when you and JJ get into a car accident. (This is the ONLY option you get if you've accepted a drink)

Dirty Deeds: Win an amateur match via disqualification - Attempt to throw your match with JJ

No Holds Barred: Win an amateur match by exploiting an injury - Go all out when fighting JJ.

Best for Business: Make a buck off a mark - Only available for a male face with 50 promo ability. Ask for cash in exchange for you autograph.

Texas Death Match: Reminisce about the most dangerous match, ever - When reminiscing about bad matches with Sagramore, remember the Texas Minefield match.

Hell in a Chapel: Reminisce about the most sacrilegious match, ever - When reminiscing about bad matches with Sagramore, remember the Brent High Chapel match.

Potato Shooter: Take the old veteran down. Or try to - Fight Sagramore for real without warning them first. Bit of a heel move.

The Cleaner: Use a mop on an opponent - Fight Sagramore for real, and use the mop while outside the ring. Automatically earns you the Legend Killer achievement if you've got 60 strength.

Legend Killer: End the career of a legend - Fight Sagramore for real. You can go with a powerbomb (you'll know their back sucks if you've tried that in the last fight), focus on their knee, or use the mop successfully (combining this with the Cleaner achievement).
Note - you also get this achievement if you maim Solitary.

Ring General: Win by making sure you lose, with style - Convince Sagramore to make the fight good. Just don't slap them, that will start a real fight.

Sell Like It's 2005: Make 'em look strong. Ridiculously strong - Oversell Sagramore's moves (requires 60 Technique).

Botch Watch: Contradict yourself in an interview - Go "the number of competitors does not matter" and later "I was glad to have less competition".

Shelton Holmes: Uncover the truth behind the Near Fall Academy eliminations - Tell the interviewer that Manoel may have been up to something the night he was escorted away. Incompatible with apologizing to Tepora.

Samoan Drop: Get one of your trainers to forgive you - Apologize to Tepora. Requires you to be nice to your Samoan friend. You also need to use whichever stat you have over 60 - talk with promo, reverse the hold with tech, muscle your way free with strength.

Super Junior: Earn Super Horns' respect early - Combines naturally with The Chosen One. Wait for him to make a move, fall on your back or break the hold in response to the Sleeper Hold, AND have at least 65 technique (setting Tepora as your mentor helps).

The Chosen One: Gain immunity in Near Fall Academy - Win the challenge against Harley and Quinn (67 in strength / promo) / hold your own against Super Horns (you need to exceed in at least one of these and do marginally well in another) AND get Tepora to forgive you.

Tough Love: Force a contestant to quit, for their own good - Get Ecstasy to quit when you catch them. (Doesn't actually matter for the further development of their romance, if you do it nicely)

Falling Star: Disgrace a contestant at Near Fall Academy - Tattle on Ecstasy. (Terminates the romance)

Lie, Cheat, Steal: Win the final Academy challenge using your wits - Use the "get a little more creative" option for the tag-team match if Ecstasy is still around. Not an option otherwise.

Show Stealer: Hog the mic - Select "I'll do the talking" when you debut with JJ. Requires 50 promo or less than 50 ring awareness.

Tron Assassin: Use a video montage to mentally massacre - Ask JJ to do the promo, and use the montage they provide.

Crooked Edge: Fall off the wagon - gustavxiii in the comments: "You have to drink before the accident, then you're automatically on the wagon. Just drink again later and fall off."

That Person Has a Family: Seek solace with your family - On the third month of your retirement, choose the "no place like home" option. *

Skull Basher: Good wrestlers don't quit—they just wear masks - Choose the "keep wrestling" option during your retirement, and be a wrestler rather than a trainer or manager. (A trainer gains Technique, a manager gains Promo, I'm fairly sure)

Super Kick Party: Gain the Super Kick, and keep it. - Per Mr. Leedles, "when you fall off the wagon pick the Cross Over as your finisher and then do a hard hitting strike style on the comeback".

Hidden Attitude: During an unmasking, use that famous line…- It was me Austin JJ.

The next four achievements correspond to the style you can pick after coming from retirement:

Gravity Forgot: Master the high-flying style

Ruler of Strong Style: Master a hard striking style.

Dead Lift: Master a style involving power moves.

1,005 Holds: Master a submission-focused style

Loser Leaves Town: Get a second chance, then fail a second time - Lose your comeback quasi-shoot (focus on the style you're weak in)

Break the Wall Down: Spear an opponent through a cage - Use the Lancelot finisher. Requires 65 strength.

What a Maneuver: Hit a high flying move from the top of a cage. - Finish your quasi-shoot with the Three Star Press or Cross Storm.

Heel Turn: Go from hero, to villain, in the eyes of the fans - Start as a babyface, but come back from your retirement as a heel.

Generation Me: Use social media to interact with fans - Reply to pretty much anyone on Twitter Toutler.

Reality Era: Air dirty laundry in public - Bring some reality into your anti-JJ promos. (You need to make that decision while debating whether to return as a face or a heel)

Kill a Wish: Be very, very mean to a child - Come back as a heel, don't bring reality subtext into your promos, go after JJ via a Make Grant a Wish kid.

2x2 Horsemen: Get into a two on two fight in the scaffolds match - Don't let JJ get eliminated before the final confrontation. Basically, if he's hanging by his fingers and you put a ladder next to him, he hangs on. Otherwise, he falls.

Handicap Match: Get into a two on one fight in the scaffolds match - Allow JJ to be eliminated. Most outcomes seem to lead to this.

Code of Honor: Turn a two on one fight into a one on one duel - Convince Superhorns to duel you 1x1. Requires 55 promo.

Bah Gawd: Take a career-ending fall - Try to fight Paul and Superhorns at once / fail the scaffold section while your energy is under 65.

Superior Junior: Get the best of Super Horns - you need at least 50 technique (or high energy) for the safest route of Keep Your Balance - Shake - Legs - Steady Myself with Cable.

Eyes on the Prize: Don't make a deal with the devil - Don't accept Paul's deal.

Pride of the Valkyrie: Get the worst misogynist in the federation to accept your challenge - Challenge Paul to a match as a woman.

Mandatory Rematch: Get a second chance at love - "Pursue Ecstasy, but don't commit when she asked about your relationship with her. Then keep pursuing her".

World's Strongest: Become a true powerhouse - Get at least 65 strength.

Excellence of Execution: Become a true mat technician - Get at least 65 Technique

Pipe Bomber: Become a true master of promos - Get at least 65 Promo ability

PlayerWinsLOL: Become the most popular wrestler in the federation - Get at least 70 favor.

Ex-cuuuuse Me: Become the most despised wrestler in the federation - Keep playing the heel to have less than 30 favor. Using the Make a Wish kid leads to a fairly huge boost.

Poetic Justice: Defeat your rival with the most appropriate finisher - Fight JJ and "set him up for a move" to finish him with the Delgado.

Not Marty: Beat your rival on the grandest stage - Fight JJ and win. You have to lose the scaffold challenge.

Not Michaels: Lose to your rival on the grandest stage - Fight JJ and lose. You have to lose the scaffold challenge. This is probably the easiest fight to win, so you have to try to lose.

The Animal: Unleash your rage on your rival - If you keep thinking about how much JJ pisses you off (throughout the game) you have the chance to "give him a thorough beating, even if that means I'm disqualified".

Kiss It Out: Prove that hate and love are two sides of the same coin - Be gay, not in a relationship, and confess your feelings to JJ after your match with them - provided you've won and weren't an ♥♥♥♥♥♥♥ to JJ throughout the game.

Heartbroken Kid: Have your heart broken on the grandest stage - JJ rejects you after your match. Confess your feeling after you've lost the match OR if your relationship isn't high enough (playing the heel is really likely to push that relationship into the negatives, but not helping JJ out throughout the game does the same).

Ultimate Opportunist: Expose a ♥♥♥♥♥ in the champion's armor, and exploit it - Put Solitary's RIGHT leg in a hold (doesn't matter whether you've been told about his medical issues)

The Beast: Cross the line, and destroy the best - " As the description suggest, destroy Solitary". You need to know about his condition, have at least 71 Ring Flash, and "go after his spine - specifically, the neck". Also gets you the Legend Killer achievement (if you didn't get it before).

Best in the World: The best match, against the best opponent, on the grandest stage - "convince Solitary to turn the match into a work." Requires at least 61 Kayfabe AND learning about his problem from Superhorns.

Our Time Is…Not Yet: Come for the King, and miss - Lose the fight with Solitary.

Fight like a Girl: Show the misogynist just how hard a woman can hit - Knock out Paul Prototype with one punch. You can do this with 61 strength and high striking ability OR with a Cross Cutter Finisher (or the equivalent custom finisher), no stats required.

Blue Pants: A crowd and a story aren't enough to beat misogyny - Lose to Prototype.

Queen of Wrestling: Become the first female GWA World Champion - Win the game as a female

Lonely Warrior: End the game still looking for closure - Fight anyone other than JJ AND don't have any romantic prospects / family support / good relationship with Alex.

Triple Threat: End the game with an unresolved love triangle - Flirt with Madison and Ecstasy both (you have to be at least somewhat into girls) (Doesn't matter what you choose at the endgame, as long as you don't decide during their first confrontation)

The Streak: End the game in the cusp of a long-term commitment - Finish the game in a relationship with Ecstasy.

Power Couple: End the game as half of the most influential couple in wrestling - Finish the game in a relationship with Madison.

Time Splitter: End the game by returning to how things used to be - Go back home AND become best friends / lovers with JJ. You obviously have to spend time with your family when you retire AND fight JJ.

Match of the Year: Receive Match of the Year honors in the Masters of Wrestling Annual World Rankings - Defeat Solitary or JJ without receiving the Beast / Animal achievement.