If A=1, B=2, C=3, etc., then T+W+O+H+U+N+D+R+E+D+A+N+D+F+I+F+T+Y+N+I+N+E = 259

CypherLiteral.cs

/// <summary>
/// brute force solution for http://www.reddit.com/r/Showerthoughts/comments/3a3xzw/if_a1_b2_c3_etc_then_twohundredandfiftynine_259/
/// Interaction logic for CypherLiteral.xaml
/// </summary>
public partial class CypherLiteral : UserControl
{
    public readonly String[] ONES = new String[]{"", 
        "ONE", "TWO", "THREE", "FOUR", "FIVE", "SIX", 
        "SEVEN", "EIGHT", "NINE"};
 
    public readonly String[] TEENS = new String[]{"TEN", 
        "ELEVEN", "TWELVE", "THIRTEEN", "FOURTEEN", 
        "FIFTEEN", "SIXTEEN", "SEVENTEEN", "EIGHTEEN", "NINETEEN"};
 
    public readonly String[] TENS = new String[]{"", 
        "TEN", "TWENTY", "THIRTY", "FORTY", "FIFTY", 
        "SIXTY", "SEVENTY", "EIGHTY", "NINETY"};
 
    public const String HUNDRED = "HUNDRED";
 
    public const String THOUSAND = "THOUSAND";
 
    public const String NEGATIVE = "NEGATIVE";
 
    public const int MAX = 9999;
 
    public CypherLiteral()
    {
        InitializeComponent();
        increment();
    }
 
    private void increment()
    {
        for (int i = -1 * MAX; i <= MAX; i++)
        {
            StringBuilder number = new StringBuilder();
 
            int num = i;
            if (num < 0)
            {
                number.Append(NEGATIVE);
                num *= -1;
            }
            if (num / 1000 > 0)
            {
                number.Append(ONES[num / 1000])
                        .Append(THOUSAND);
                num %= 1000;
            }
            if (num / 100 > 0)
            {
                number.Append(ONES[num / 100])
                        .Append(HUNDRED);
                num %= 100;
            }
            if (num > 10 && num < 20)
            {
                number.Append(TEENS[num % 10]);
            }
            else if (num > 0)
            {
                number.Append(TENS[num / 10])
                        .Append(ONES[num % 10]);
            }
 
            int sum = SumChars(number.ToString());
            int delta = Math.Abs(sum - Math.Abs(i));
            if (delta <= 2)
                txtOut.Text += string.Format(", {0} = {1}({2})", number.ToString(), SumChars(number.ToString()), delta);
        }
    }
 
    int SumChars(string chars)
    {
        int sum = 0;
        for (int i = 0; i < chars.Length; i++)
        {
            sum += chars[i] - 'A' + 1;
        }
        return sum;
    }
}