My .pryrc file

.pryrc

# === EDITOR ===
Pry.editor = 'vi'
require 'awesome_print'

# == Pry-Nav - Using pry as a debugger ==
Pry.commands.alias_command 'c', 'continue' rescue nil
Pry.commands.alias_command 's', 'step' rescue nil
Pry.commands.alias_command 'n', 'next' rescue nil

# === CUSTOM PROMPT ===
# This prompt shows the ruby version (useful for RVM)
# Pry.prompt = [proc { |obj, nest_level, _| "#{RUBY_VERSION} (#{obj}):#{nest_level} > " }, proc { |obj, nest_level, _| "#{RUBY_VERSION} (#{obj}):#{nest_level} * " }]
BLACK = "\001\e[0;30m\002"
WHITE = "\001\e[0m\002"
Pry.prompt = [
    proc { |target_self, nest_level, pry|
      line_num = pry.input_array.size
      prompt = "#{line_num} "
      "#{BLACK}#{prompt}#{WHITE}"
    },
    proc { |target_self, nest_level, pry|
      prompt = ". "
      "#{BLACK}#{prompt}#{WHITE}"
    }
  ]
    

# === Listing config ===
# Better colors - by default the headings for methods are too 
# similar to method name colors leading to a "soup"
# These colors are optimized for use with Solarized scheme 
# for your terminal
Pry.config.ls.separator = "\n" # new lines between methods
Pry.config.ls.heading_color = :magenta
Pry.config.ls.public_method_color = :green
Pry.config.ls.protected_method_color = :yellow
Pry.config.ls.private_method_color = :bright_black

# == PLUGINS ===
# awesome_print gem: great syntax colorized printing
# look at ~/.aprc for more settings for awesome_print
begin
  require 'awesome_print'
  # The following line enables awesome_print for all pry output,
  # and it also enables paging
  Pry.config.print = proc { |output, value|
    formatted = value.ai
    value.ai.split("\n").each_with_index do |v, i|
      prefix = (i == 0) ? "=>" : '. '
      output.puts "#{BLACK}#{prefix}#{WHITE} #{v}"
    end
    # output.puts formatted
    # Pry::Helpers::BaseHelpers.stagger_output("#{BLACK}=>#{WHITE} #{value.ai}", output)
  }

  # If you want awesome_print without automatic pagination, use the line below
  # Pry.config.print = proc { |output, value| output.puts value.ai }
rescue LoadError => err
  puts "gem install awesome_print  # <-- highly recommended"
end

# === CUSTOM COMMANDS ===
# from: https://gist.github.com/1297510
default_command_set = Pry::CommandSet.new do
  command "copy", "Copy argument to the clip-board" do |str|
     IO.popen('pbcopy', 'w') { |f| f << str.to_s }
  end

  command "clear" do
    system 'clear'
    if ENV['RAILS_ENV']
      output.puts "Rails Environment: " + ENV['RAILS_ENV']
    end
  end

  command "sql", "Send sql over AR." do |query|
    if ENV['RAILS_ENV'] || defined?(Rails)
      pp ActiveRecord::Base.connection.select_all(query)
    else
      pp "No rails env defined"
    end
  end
  command "caller_method" do |depth|
    depth = depth.to_i || 1
    if /^(.+?):(\d+)(?::in `(.*)')?/ =~ caller(depth+1).first
      file   = Regexp.last_match[1]
      line   = Regexp.last_match[2].to_i
      method = Regexp.last_match[3]
      output.puts [file, line, method]
    end
  end
end

Pry.config.commands.import default_command_set


# === CONVENIENCE METHODS ===
# Stolen from https://gist.github.com/807492
# Use Array.toy or Hash.toy to get an array or hash to play with
class Array
  def self.toy(n=10, &block)
    block_given? ? Array.new(n,&block) : Array.new(n) {|i| i+1}
  end
end

class Hash
  def self.toy(n=10)
    Hash[Array.toy(n).zip(Array.toy(n){|c| (96+(c+1)).chr})]
  end
end

# === COLOR CUSTOMIZATION ===
# Everything below this line is for customizing colors, you have to use the ugly
# color codes, but such is life. 
CodeRay.scan("example", :ruby).term # just to load necessary files
# Token colors pulled from: https://github.com/rubychan/coderay/blob/master/lib/coderay/encoders/terminal.rb

$LOAD_PATH << File.dirname(File.realpath(__FILE__))

# In CodeRay >= 1.1.0 token colors are defined as pre-escaped ANSI codes
if Gem::Version.new(CodeRay::VERSION) >= Gem::Version.new('1.1.0')
  require "escaped_colors"
else
  require "unescaped_colors"
end

module CodeRay
  module Encoders
    class Terminal < Encoder
      # override old colors
      TERM_TOKEN_COLORS.each_pair do |key, value|
        TOKEN_COLORS[key] = value
      end
    end
  end
end

The require 'awesome_print' at L43 will get rescued if it fails, but the one on L3 won't and obviously it gets hit first