diff --git a/src/Discord.Net.Core/Entities/Roles/IRole.cs b/src/Discord.Net.Core/Entities/Roles/IRole.cs
index aa34fb019..2e3d63702 100644
--- a/src/Discord.Net.Core/Entities/Roles/IRole.cs
+++ b/src/Discord.Net.Core/Entities/Roles/IRole.cs
@@ -4,7 +4,7 @@ using System.Threading.Tasks;
 
 namespace Discord
 {
-    public interface IRole : ISnowflakeEntity, IDeletable, IMentionable
+    public interface IRole : ISnowflakeEntity, IDeletable, IMentionable, IComparable<IRole>
     {
         /// <summary> Gets the guild owning this role.</summary>
         IGuild Guild { get; }
@@ -27,4 +27,4 @@ namespace Discord
         ///// <summary> Modifies this role. </summary>
         Task ModifyAsync(Action<ModifyGuildRoleParams> func, RequestOptions options = null);
     }
-}
\ No newline at end of file
+}
diff --git a/src/Discord.Net.Core/Entities/Users/IGuildUser.cs b/src/Discord.Net.Core/Entities/Users/IGuildUser.cs
index b48c76a37..139640e5a 100644
--- a/src/Discord.Net.Core/Entities/Users/IGuildUser.cs
+++ b/src/Discord.Net.Core/Entities/Users/IGuildUser.cs
@@ -6,7 +6,7 @@ using System.Threading.Tasks;
 namespace Discord
 {
     /// <summary> A Guild-User pairing. </summary>
-    public interface IGuildUser : IUser, IVoiceState
+    public interface IGuildUser : IUser, IVoiceState, IComparable<IGuildUser>
     {
         /// <summary> Gets when this user joined this guild. </summary>
         DateTimeOffset? JoinedAt { get; }
diff --git a/src/Discord.Net.Core/Extensions/GuildUserExtensions.cs b/src/Discord.Net.Core/Extensions/GuildUserExtensions.cs
index 57d6a13dc..51e00fb42 100644
--- a/src/Discord.Net.Core/Extensions/GuildUserExtensions.cs
+++ b/src/Discord.Net.Core/Extensions/GuildUserExtensions.cs
@@ -15,5 +15,17 @@ namespace Discord
             => RemoveRolesAsync(user, (IEnumerable<IRole>)roles);
         public static Task RemoveRolesAsync(this IGuildUser user, IEnumerable<IRole> roles)
             => user.ModifyAsync(x => x.RoleIds = user.RoleIds.Except(roles.Select(y => y.Id)).ToArray());
+
+        public static IEnumerable<IRole> GetRoles(this IGuildUser user) {
+            var guild = user.Guild;
+            return user.RoleIds.Select(r => guild.GetRole(r));
+        }
+
+        internal static int Compare(this IGuildUser u1, IGuildUser u2) {
+            var r1 = u1.GetRoles().Max();
+            var r2 = u2.GetRoles().Max();
+            var result = r1.CompareTo(r2);
+            return result != 0 ? result : u1.Id.CompareTo(u2.Id);
+        }
     }
 }
diff --git a/src/Discord.Net.Rest/Entities/Roles/RestRole.cs b/src/Discord.Net.Rest/Entities/Roles/RestRole.cs
index 6e81ce9df..60d868caa 100644
--- a/src/Discord.Net.Rest/Entities/Roles/RestRole.cs
+++ b/src/Discord.Net.Rest/Entities/Roles/RestRole.cs
@@ -4,9 +4,7 @@ using System.Diagnostics;
 using System.Threading.Tasks;
 using Model = Discord.API.Role;
 
-namespace Discord.Rest
-{
-    [DebuggerDisplay(@"{DebuggerDisplay,nq}")]
+namespace Discord.Rest { [DebuggerDisplay(@"{DebuggerDisplay,nq}")]
     public class RestRole : RestEntity<ulong>, IRole
     {
         public RestGuild Guild { get; }
@@ -51,10 +49,12 @@ namespace Discord.Rest
         public Task DeleteAsync(RequestOptions options = null)
             => RoleHelper.DeleteAsync(this, Discord, options);
 
+
         public override string ToString() => Name;
         private string DebuggerDisplay => $"{Name} ({Id})";
 
         //IRole
         IGuild IRole.Guild => Guild;
+        public int CompareTo(IRole role) => Position.CompareTo(role.Position);
     }
 }
diff --git a/src/Discord.Net.Rest/Entities/Users/RestGuildUser.cs b/src/Discord.Net.Rest/Entities/Users/RestGuildUser.cs
index 180ad38bc..6e242e264 100644
--- a/src/Discord.Net.Rest/Entities/Users/RestGuildUser.cs
+++ b/src/Discord.Net.Rest/Entities/Users/RestGuildUser.cs
@@ -96,6 +96,8 @@ namespace Discord.Rest
                 throw new InvalidOperationException("Unable to return this entity's parent unless it was fetched through that object.");
             }
         }
+    
+        public int CompareTo(IGuildUser user) => this.Compare(user);
 
         //IVoiceState
         bool IVoiceState.IsSelfDeafened => false;
@@ -103,5 +105,6 @@ namespace Discord.Rest
         bool IVoiceState.IsSuppressed => false;
         IVoiceChannel IVoiceState.VoiceChannel => null;
         string IVoiceState.VoiceSessionId => null;
+
     }
 }
diff --git a/src/Discord.Net.WebSocket/Entities/Roles/SocketRole.cs b/src/Discord.Net.WebSocket/Entities/Roles/SocketRole.cs
index 515389da1..d6612dcb6 100644
--- a/src/Discord.Net.WebSocket/Entities/Roles/SocketRole.cs
+++ b/src/Discord.Net.WebSocket/Entities/Roles/SocketRole.cs
@@ -57,5 +57,6 @@ namespace Discord.WebSocket
 
         //IRole
         IGuild IRole.Guild => Guild;
+        public int CompareTo(IRole role) => Position.CompareTo(role.Position);
     }
 }
diff --git a/src/Discord.Net.WebSocket/Entities/Users/SocketGuildUser.cs b/src/Discord.Net.WebSocket/Entities/Users/SocketGuildUser.cs
index 5a670c14d..3610b6284 100644
--- a/src/Discord.Net.WebSocket/Entities/Users/SocketGuildUser.cs
+++ b/src/Discord.Net.WebSocket/Entities/Users/SocketGuildUser.cs
@@ -96,6 +96,7 @@ namespace Discord.WebSocket
         IGuild IGuildUser.Guild => Guild;
         ulong IGuildUser.GuildId => Guild.Id;
         IReadOnlyCollection<ulong> IGuildUser.RoleIds => RoleIds;
+        public int CompareTo(IGuildUser user) => this.Compare(user);
 
         //IUser
         Task<IDMChannel> IUser.GetDMChannelAsync(CacheMode mode, RequestOptions options)