diff --git a/src/plugins/Utility.ts b/src/plugins/Utility.ts
index 3f1a98d7..408276a3 100644
--- a/src/plugins/Utility.ts
+++ b/src/plugins/Utility.ts
@@ -1,5 +1,5 @@
 import { decorators as d } from "knub";
-import { Channel, EmbedOptions, Member, Message, TextChannel, User, VoiceChannel } from "eris";
+import { Channel, EmbedOptions, Member, Message, Role, TextChannel, User, VoiceChannel } from "eris";
 import {
   chunkArray,
   embedPadding,
@@ -87,32 +87,73 @@ export class UtilityPlugin extends ZeppelinPlugin {
     }
   }
 
-  @d.command("roles", "[search:string$]")
+  @d.command("roles", "[search:string$]", {
+    options: [
+      {
+        name: "counts",
+        type: "bool",
+      },
+    ],
+  })
   @d.permission("roles")
-  async rolesCmd(msg: Message, args: { search?: string }) {
-    let roles = (msg.channel as TextChannel).guild.roles.map(role => `${role.name} ${role.id}`);
+  async rolesCmd(msg: Message, args: { search?: string; counts?: boolean }) {
+    let roles: Array<{ _memberCount?: number } & Role> = Array.from((msg.channel as TextChannel).guild.roles.values());
     if (args.search) {
       const searchStr = args.search.toLowerCase();
-      roles = roles.filter(r => r.toLowerCase().includes(searchStr));
+      roles = roles.filter(r => r.name.toLowerCase().includes(searchStr) || r.id === searchStr);
     }
 
-    roles.sort((a, b) => {
-      if (a.toLowerCase() > b.toLowerCase()) return 1;
-      if (a.toLowerCase() < b.toLowerCase()) return -1;
-      return 0;
-    });
+    if (args.counts) {
+      // If the user requested role member counts as well, calculate them and sort the roles by their member count
+      const roleCounts: Map<string, number> = Array.from(this.guild.members.values()).reduce((map, member) => {
+        for (const roleId of member.roles) {
+          if (!map.has(roleId)) map.set(roleId, 0);
+          map.set(roleId, map.get(roleId) + 1);
+        }
+
+        return map;
+      }, new Map());
+
+      // The "everyone" role always has all members in it
+      roleCounts.set(this.guildId, this.guild.memberCount);
+
+      for (const role of roles) {
+        role._memberCount = roleCounts.has(role.id) ? roleCounts.get(role.id) : 0;
+      }
+
+      roles.sort((a, b) => {
+        if (a._memberCount > b._memberCount) return -1;
+        if (a._memberCount < b._memberCount) return 1;
+        return 0;
+      });
+    } else {
+      // Otherwise sort by name
+      roles.sort((a, b) => {
+        if (a.name.toLowerCase() > b.name.toLowerCase()) return 1;
+        if (a.name.toLowerCase() < b.name.toLowerCase()) return -1;
+        return 0;
+      });
+    }
 
     const chunks = chunkArray(roles, 20);
     for (const [i, chunk] of chunks.entries()) {
+      const roleLines = chunk.map(role => {
+        let line = `${role.id} ${role.name}`;
+        if (role._memberCount != null) {
+          line += role._memberCount === 1 ? ` (${role._memberCount} member)` : ` (${role._memberCount} members)`;
+        }
+        return line;
+      });
+
       if (i === 0) {
         msg.channel.createMessage(
           trimLines(`
           ${args.search ? "Total roles found" : "Total roles"}: ${roles.length}
-          \`\`\`py\n${chunk.join("\n")}\`\`\`
+          \`\`\`py\n${roleLines.join("\n")}\`\`\`
         `),
         );
       } else {
-        msg.channel.createMessage("```py\n" + chunk.join("\n") + "```");
+        msg.channel.createMessage("```py\n" + roleLines.join("\n") + "```");
       }
     }
   }