Best way to parse string of email addresses

At the risk of creating two problems, you could create a regular expression that matches any of your email formats. Use "|" to separate the formats within this one regex. Then you can run it over your input string and pull out all of the matches.

public class Address
{
    private string _first;
    private string _last;
    private string _name;
    private string _domain;

    public Address(string first, string last, string name, string domain)
    {
        _first = first;
        _last = last;
        _name = name;
        _domain = domain;
    }

    public string First
    {
        get { return _first; }
    }

    public string Last
    {
        get { return _last; }
    }

    public string Name
    {
        get { return _name; }
    }

    public string Domain
    {
        get { return _domain; }
    }
}

[TestFixture]
public class RegexEmailTest
{
    [Test]
    public void TestThreeEmailAddresses()
    {
        Regex emailAddress = new Regex(
            @"((?<last>\w*), (?<first>\w*) <(?<name>\w*)@(?<domain>\w*\.\w*)>)|" +
            @"((?<first>\w*) (?<last>\w*) <(?<name>\w*)@(?<domain>\w*\.\w*)>)|" +
            @"((?<name>\w*)@(?<domain>\w*\.\w*))");
        string input = "First, Last <[email protected]>, [email protected], First Last <[email protected]>";

        MatchCollection matches = emailAddress.Matches(input);
        List<Address> addresses =
            (from Match match in matches
             select new Address(
                 match.Groups["first"].Value,
                 match.Groups["last"].Value,
                 match.Groups["name"].Value,
                 match.Groups["domain"].Value)).ToList();
        Assert.AreEqual(3, addresses.Count);

        Assert.AreEqual("Last", addresses[0].First);
        Assert.AreEqual("First", addresses[0].Last);
        Assert.AreEqual("name", addresses[0].Name);
        Assert.AreEqual("domain.com", addresses[0].Domain);

        Assert.AreEqual("", addresses[1].First);
        Assert.AreEqual("", addresses[1].Last);
        Assert.AreEqual("name", addresses[1].Name);
        Assert.AreEqual("domain.com", addresses[1].Domain);

        Assert.AreEqual("First", addresses[2].First);
        Assert.AreEqual("Last", addresses[2].Last);
        Assert.AreEqual("name", addresses[2].Name);
        Assert.AreEqual("domain.com", addresses[2].Domain);
    }
}

There are several down sides to this approach. One is that it doesn't validate the string. If you have any characters in the string that don't fit one of your chosen formats, then those characters are just ignored. Another is that the accepted formats are all expressed in one place. You cannot add new formats without changing the monolithic regex.

There is internal System.Net.Mail.MailAddressParser class which has method ParseMultipleAddresses which does exactly what you want. You can access it directly through reflection or by calling MailMessage.To.Add method, which accepts email list string.

private static IEnumerable<MailAddress> ParseAddress(string addresses)
{
    var mailAddressParserClass = Type.GetType("System.Net.Mail.MailAddressParser");
    var parseMultipleAddressesMethod = mailAddressParserClass.GetMethod("ParseMultipleAddresses", System.Reflection.BindingFlags.NonPublic | System.Reflection.BindingFlags.Static);
    return (IList<MailAddress>)parseMultipleAddressesMethod.Invoke(null, new object[0]);
}


    private static IEnumerable<MailAddress> ParseAddress(string addresses)
    {
        MailMessage message = new MailMessage();
        message.To.Add(addresses);
        return new List<MailAddress>(message.To); //new List, because we don't want to hold reference on Disposable object
    }

There isn't really an easy solution to this. I would recommend making a little state machine that reads char-by-char and do the work that way. Like you said, splitting by comma won't always work.

A state machine will allow you to cover all possibilities. I'm sure there are many others you haven't seen yet. For example: "First Last"

Look for the RFC about this to discover what all the possibilities are. Sorry, I don't know the number. There are probably multiple as this is the kind of things that evolves.