Getting right down to business, you will start your playthrough on the hard difficulty. As a general note, there are several achievements in the walkthrough that are not explained as to how you unlock them. Don't worry, those achievements will unlock as you progress through the story!
Chapter 1 - There are no Playboy magazines in this chapter.
Chapter 2 - After you help your sister, start walking down to Joe's place. On the right side of the road you'll see a couple yelling at each other while a man is trying to fix his car. Wait until he gets fed up and leaves the woman all alone. Then go over and fix the car for her by pressing the X button. See the video below for the locations of the Playboy magazines. Now just continue playing through the rest of the chapter.
Chapter 3 - See the video guide below for "The Professional" achievement and the other video for the locations of the Playboy magazines in this chapter. When you are told to deliver the gas stamps, deliver the maximum amount of stamps before time runs out. If you don't make it, don't worry, after you beat the game you can play this on easy difficulty which will give you more time.
Sell all the gas stamps before the time runs out.
Chapter 4 - No missable achievements other than the Playboys, video guide below.
Chapter 5 - See the video guide below for the Playboy locations. This is the chapter that I unlocked the achievement for killing 50 enemies. If you don't unlock it here, you will soon after. When you are using the "Buzzsaw", make sure to kill all of the enemies by shooting them in the head. When you kill 5 enemies in a row by headshots, you'll unlock an achievement.
Kill 5 enemies in rapid succession with a headshot.
Chapter 6 - Playboy guide below.
Chapter 7 - Playboy guide below.
Chapter 8 - Playboy guide below.
Chapter 9 - The Playboy guide is below. When you are told to change your clothes, go down the road to the clothing store that it shows on your map and buy a luxury suit.
Chapter 10 - The Playboy guide is below.
Chapter 11 - The Playboy guide is below. When it is time to get Leo out of his house, you will need to escape without being caught in order to unlock an achievement. A video guide for this can be found below. Also, the achievement "End Of The Rainbow" is missable, although I unlocked it just by playing through it naturally. When you make your assault on the bar after you have finished destroying everything, they will tell you to exit through the back door. Once you leave, you will see a guy get into his car and try to drive away. Make sure you kill this guy before he escapes for the achievement.
Wake Up Call
Help Leo out of a tricky situation without getting caught.
Chapter 12 - The Playboy guide is below.
Chapter 13 - The Playboy guide is below.
Chapter 14 - The Playboy guide is below.
Chapter 15 - The Playboy guide is below.
Finish the story on Medium difficulty level or higher.
Finish the story on Hard difficulty level.
It's time for the wanted posters! I'm giving you two guides to work with. The first one, from Achievement Hunter, is the guide you should use first. I recommend using the second if you miss any of the posters. At the main menu if you select extras, then collectables, and then wanted posters, you can see which ones you have as well as the ones you don't have. The second guide shows you what the posters real numbers are. The Achievement Hunter guide doesn't have the proper numbers, but is better put together. While you are collecting the posters, use the same car to collect all of them. If your car starts going very slow, it probably means you need to refuel it. To check how many miles you have on your car, take it to your garage and store it, then reopen the garage and pull up your car and it will tell you in the stats.
Time for the mop-up!
You don't have to use this specific car, you can use any fast car.
Get Rich or Die Flyin’
Get all wheels of your car into the air for at least 20 meters and then touch the ground again.
Mike Bruski's scrapyard is on the map. Go there and use his car crusher to crush 5 different vehicles. He will also give you money for the scrap metal.
If you load up the chapter "Sea Gift", you'll get a phone call, and then you can go about your business. You don't have to go see whats-his-name (Henry). Instead just cruise around and find some luxury cars and bring them to Derek at the docks. Bring him 5 good cars for an achievement.
Sell 5 vehicles to Derek at the dock.
Load up Chapter 11. Play until you get to the point right after you save Leo from his house and he wants you to take him to the train station. Instead of taking him, go to the nearest body shop. Once you're there, upgrade the engine two times. This will bank you two achievements, but that isn't all. Next, go to that big bridge in the middle of the map and floor it baby! You will get an achievement when you bring your car to 125mi/h. There's a video guide below, just in case you don't know what I'm talking about.
Now head down to the docks and start beating the piss out of the dock workers! Once you kill 30 people you will get the next achievement.
Kill a total of 30 enemies using melee attacks.
Find yourself an armored car and make your way towards Bruski's scrapyard. Once you are almost there go on a rampage and bring up your wanted level to 4 stars. Now get in the armored car and go into Bruski's car crusher while the cops are on your tail. Now sit there, for ten minutes. *Yawn*
Hard to Kill
The police want you dead. Survive for 10 minutes!
You know those vehicles that you stay away from. The ones like: the ice cream truck, rig, police bus, and hearse. Drive these. If you haven't yet unlocked the achievement for driving 30 different cars, try loading up the chapter before you go to prison that has all of those crappy cars. Drive a few of them and you should have the achievement for driving 30 different cars.
See the video guide for the achievement "Cruise Control". Just make sure to stay at about 40 miles per hour.
Keep any vehicle at 30 mph or over for 5 or more minutes.
For the next achievement you have to rob 5 stores in 5 minutes. Find a good route, and when you are doing this, try to stay away from diners because they are always full of gangsters. The best places to rob are the gas stations and gun stores. See the video guide below.
Rob 5 stores in under 5 minutes.